(R)-5-chloro-2-(5-methyl-1,4-diazepan-1-yl)benzo[d]oxazole

Base Information

• Chemical Name: (R)-5-chloro-2-(5-methyl-1,4-diazepan-1-yl)benzo[d]oxazole
• CAS No.: 1266975-27-2
• Molecular Formula: C13H16ClN3O
• Molecular Weight: 265.743
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID60693235
• Nikkaji Number: J3.100.094G
• Wikidata: Q72451665
• Mol file: 1266975-27-2.mol

Synonyms:1266975-27-2;(R)-5-chloro-2-(5-methyl-1,4-diazepan-1-yl)benzo[d]oxazole;5-Chloro-2-[(5R)-5-methyl-1,4-diazepan-1-yl]-1,3-benzoxazole;5-Chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole;SCHEMBL13735931;DTXSID60693235;RADJSLVGESASMK-SECBINFHSA-N;AMY38841;BCP14129;CS-M1403;MFCD22124911;Benzoxazole, 5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]-;AS-39000;2-[(5R)-5-Methylhexahydro-1H-1,4-diazepine-1-yl]-5-chlorobenzoxazole

Chemical Property of (R)-5-chloro-2-(5-methyl-1,4-diazepan-1-yl)benzo[d]oxazole

Chemical Property:

• Boiling Point: 395℃
• PKA: 10.18±0.40(Predicted)
• Flash Point: 193℃
• PSA: 41.30000
• Density: 1.221
• LogP: 3.06320
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 265.0981898
• Heavy Atom Count: 18
• Complexity: 291

Purity/Quality:

98%,99%, ^*data from raw suppliers

(R)-5-chloro-2-(5-Methyl-1,4-diazepan-1-yl)benzo[d]oxazole 97 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCN(CCN1)C2=NC3=C(O2)C=CC(=C3)Cl
• Isomeric SMILES: C[C@@H]1CCN(CCN1)C2=NC3=C(O2)C=CC(=C3)Cl

Technology Process of (R)-5-chloro-2-(5-methyl-1,4-diazepan-1-yl)benzo[d]oxazole

There total 8 articles about (R)-5-chloro-2-(5-methyl-1,4-diazepan-1-yl)benzo[d]oxazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

5-chloro-2-mercaptobenzoxazole (22876-19-3) → 5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole (1266975-27-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 1.75 h / 25 °C / Industry scale

1.2: 2.5 h / 10 - 20 °C

1.3: 10 h / 20 °C

2.1: hydrogenchloride; water / 10 h / 20 - 30 °C

2.2: 35 °C / pH > 10

2.3: 24 h / -5 °C / Inert atmosphere

With hydrogenchloride; oxalyl dichloride; water; N,N-dimethyl-formamide; In dichloromethane;

Reference yield:

methanesulfonic acid 2-[(5-chloro-benzooxazol-2-yl)-(3-oxo-butyl)amino]ethyl ester (1383717-11-0) → 5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole (1266975-27-2) + C14H20ClN3O4S (1383717-12-1)

Guidance literature:

With triethanolamine; sitagliptin transaminase CDX-017; pyridoxal 5'-phosphate; isopropylamine hydrochloride; In water; dimethyl sulfoxide; at 40 ℃; pH=9.5; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ol3014123

Reference yield:

methanesulfonic acid 2-[(5-chloro-benzooxazol-2-yl)-(3-oxo-butyl)amino]ethyl ester (1383717-11-0) → C13H16ClN3O + 5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole (1266975-27-2) + C14H20ClN3O4S (1383717-12-1)

Guidance literature:

With triethanolamine; sitagliptin transaminase CDX-017; pyridoxal 5'-phosphate; isopropylamine hydrochloride; In water; dimethyl sulfoxide; at 40 ℃; pH=8.5; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ol3014123

upstream raw materials:

2-bromo-5-chlorobenzo[d]oxazole

2-[(5-chloro-1,3-benzoxazol-2-yl)amino]ethanol

C₁₃H₁₅ClN₂O₃

methanesulfonic acid 2-[(5-chloro-benzooxazol-2-yl)-(3-oxo-butyl)amino]ethyl ester

Downstream raw materials:

Suvorexant

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF AN OREXIN RECEPTOR ANTAGONIST". . . Retrieved 2012/11/13.