Water → HCID 89874579, compound

HRID 715245Notes

Reaction equation

HRID 715245 reaction equation
[Cl:1][C:2]1[C:7]2[CH2:8][NH:9][C:10](=[O:11])[C:6]=2[CH:5]=[C:4]([CH3:12])[N:3]=1.Cl[CH2:14][C:15]1[CH:16]=[C:17]([CH3:27])[C:18]([O:21][CH2:22][C:23]([F:26])([F:25])[F:24])=[N:19][CH:20]=1.[H-].[Na+].O>CC(N(C)C)=O>[Cl:1][C:2]1[C:7]2[CH2:8][N:9]([CH2:14][C:15]3[CH:20]=[N:19][C:18]([O:21][CH2:22][C:23]([F:26])([F:25])[F:24])=[C:17]([CH3:27])[CH:16]=3)[C:10](=[O:11])[C:6]=2[CH:5]=[C:4]([CH3:12])[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 67508778HCID 67508778, compoundHCID 89875540HCID 89875540, compound

Product 1

HCID 89874579HCID 89874579, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 4-chloro-6-methyl-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one (91 mg, 0.50 mmol, Step-1), 5-(chloromethyl)-3-methyl-2-(2,2,2-trifluoroethoxy)pyridine (119 mg, 0.50 mmol, Step-3 in Amine-3) and sodium hydride (40 mg, 0.99 mmol) in DMA (1.7 mL) is stirred for 1 hour at rt. The reaction mixture is poured into water and extracted with EtOAc. The organic layer is dried over sodium sulfate. After filtration, the filtrate and volatiles are removed. The residue is purified by column chromatography on silica gel eluting with n-hexane/EtOAc (2:1) to give 65 mg (34% yield) of the title compound as colorless oil.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. filtrationAfter filtration
  4. customthe filtrate and volatiles are removed
  5. customThe residue is purified by column chromatography on silica gel eluting with n-hexane/EtOAc (2:1)

Sources & evidence

ORD record
ord-d248fbbcd07942f59477e60e3fe2fc1f
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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