(R)-3-chloro-7-(2-(hydroxymethyl)morpholino)-2-methyl-5-(trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile

Base Information

• Chemical Name: (R)-3-chloro-7-(2-(hydroxymethyl)morpholino)-2-methyl-5-(trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile
• CAS No.: 2227425-05-8
• Molecular Formula: C₁₅H₁₄ClF₃N₄O₂
• Molecular Weight: 374.75
• Mol file: 2227425-05-8.mol

Synonyms:

Chemical Property of (R)-3-chloro-7-(2-(hydroxymethyl)morpholino)-2-methyl-5-(trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile

Chemical Property:

• Boiling Point: 599.2±50.0 °C(Predicted)
• Density: 1.57±0.1 g/cm3(Predicted)

Purity/Quality:

99%+, ^*data from raw suppliers

PF-06869206 >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: PF-06869206 is an orally bioavailable inhibitor of sodium-phosphate cotransporter 2a (NaPi2a; IC50 = 380 nM). It is selective for NaPi2a over NaPi2b, NaPi2c, PiT-1, and PiT-2 (IC50s = >25 μM).

Technology Process of (R)-3-chloro-7-(2-(hydroxymethyl)morpholino)-2-methyl-5-(trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile

There total 10 articles about (R)-3-chloro-7-(2-(hydroxymethyl)morpholino)-2-methyl-5-(trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile 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: 84.0%

3,7-dichloro-2-methyl-5-(trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile + (S)-morpholin-2-ylmethanol (132073-83-7) → (S)-3-chloro-7-(2-(hydroxymethyl)morpholino)-2-methyl-5-(trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile (2227425-05-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 80 ℃; for 18h;

DOI:10.1021/acsmedchemlett.8b00013

Reference yield: 15.0%

7-chloro-2-methyl-5-(trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile (1268521-89-6) + (2R)-2-hydroxymethylmorpholine (156925-22-3) → (R)-3-chloro-7-(2-(hydroxymethyl)morpholino)-2-methyl-5-(trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile (2227425-05-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; cesium fluoride; In dimethyl sulfoxide; at 120 ℃; for 16h;

DOI:10.1021/acsmedchemlett.8b00013

Reference yield:

diethyl (E)-2-((1-cyanoprop-1-en-2-yl)amino)malonate → (S)-3-chloro-7-(2-(hydroxymethyl)morpholino)-2-methyl-5-(trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile (2227425-05-8)

Guidance literature:

Multi-step reaction with 6 steps

1: sodium ethanolate / ethanol / 16 h / 37 - 80 °C / Large scale

2: N-ethyl-N,N-diisopropylamine / acetonitrile / 1.5 h / -10 - -5 °C / Large scale

3: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 20 h / 90 °C / Large scale

4: trichlorophosphate / acetonitrile / 16 h / 0 - 60 °C

5: N-chloro-succinimide / N,N-dimethyl-formamide / 3 h / 30 °C

6: N-ethyl-N,N-diisopropylamine / acetonitrile / 18 h / 80 °C

With N-chloro-succinimide; sodium ethanolate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; trichlorophosphate; In ethanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/acsmedchemlett.8b00013

upstream raw materials:

ethyl 3-amino-5-methyl-1H-pyrrole-2-carboxylate

7-hydroxy-2-methyl-5-(trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile

(S)-morpholin-2-ylmethanol

7-chloro-2-methyl-5-(trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile

Refernces