L-Alaninol → N-((S)-1-hydroxypropan-2-yl)-2-(1-(5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)-1-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-4-carboxamide

HRID 715486Notes

Reaction equation

HRID 715486 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:14]([N:16]2[C:24](=[O:25])[C:23]3[CH:22]=[CH:21][N:20]=[C:19]([C:26](OC4C=CC=CC=4)=[O:27])[C:18]=3[CH2:17]2)[CH3:15])[CH:5]=[N:6][C:7]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11].[NH2:35][C@@H:36]([CH3:39])[CH2:37][OH:38]>C1COCC1>[OH:38][CH2:37][C@@H:36]([NH:35][C:26]([C:19]1[C:18]2[CH2:17][N:16]([CH:14]([C:4]3[CH:5]=[N:6][C:7]([O:8][CH2:9][C:10]([F:13])([F:11])[F:12])=[C:2]([CH3:1])[CH:3]=3)[CH3:15])[C:24](=[O:25])[C:23]=2[CH:22]=[CH:21][N:20]=1)=[O:27])[CH3:39]

Participants

4

Reactant 2

HCID 80307L-AlaninolHCID 89875412phenyl 2-(1-(5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)-1-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-4-carboxylate

Product 1

HCID 89874554N-((S)-1-hydroxypropan-2-yl)-2-(1-(5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)-1-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-4-carboxamideYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of phenyl 2-(1-(5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)-1-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-4-carboxylate (20 mg, 0.042 mmol, Intermediate-91, single enantiomer) and (S)-2-aminopropan-1-ol in THF (1.0 mL) is heated at 90° C. overnight. The reaction mixture is concentrated. The residue is purified by preparative LC-MS to give 9.9 mg (52% yield) of the title compound.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customThe residue is purified by preparative LC-MS

Sources & evidence

ORD record
ord-7ceb700fbfbb4ff9b1fdcf5ff47e3e80
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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