Morpholine → HCID 89874665, compound

HRID 715485Notes

Reaction equation

HRID 715485 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[C:11]2[CH2:12][N:13]([CH:16]([C:18]3[CH:19]=[N:20][C:21]([O:25][CH2:26][C:27]([F:30])([F:29])[F:28])=[C:22]([CH3:24])[CH:23]=3)[CH3:17])[C:14](=[O:15])[C:10]=2[CH:9]=[CH:8][N:7]=1)=[O:4].[NH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1>CN(C=O)C>[CH3:24][C:22]1[CH:23]=[C:18]([CH:16]([N:13]2[C:14](=[O:15])[C:10]3[CH:9]=[CH:8][N:7]=[C:6]([NH:5][C:3](=[O:4])[CH2:2][N:31]4[CH2:36][CH2:35][O:34][CH2:33][CH2:32]4)[C:11]=3[CH2:12]2)[CH3:17])[CH:19]=[N:20][C:21]=1[O:25][CH2:26][C:27]([F:28])([F:30])[F:29]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 89874143HCID 89874143, compound

Product 1

HCID 89874665HCID 89874665, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-chloro-N-(2-(1-(5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)-1-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-4-yl)acetamide (25 mg, 0.056 mmol, Step-1, single enantiomer), and morpholine (15 mg, 0.17 mmol) in DMF (1.0 mL) is heated at 60° C. for 3 hours. The reaction mixture is concentrated. The residue is purified by preparative LC-MS to give 10.6 mg (38% 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-cfef81a31144476681ab130bab5233a9
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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