Pyridine → HCID 89874143, compound

HRID 715265Notes

Reaction equation

HRID 715265 reaction equation
[NH2:1][C:2]1[C:7]2[CH2:8][N:9]([CH:12]([C:14]3[CH:15]=[N:16][C:17]([O:21][CH2:22][C:23]([F:26])([F:25])[F:24])=[C:18]([CH3:20])[CH:19]=3)[CH3:13])[C:10](=[O:11])[C:6]=2[CH:5]=[CH:4][N:3]=1.N1C=CC=CC=1.[Cl:33][CH2:34][C:35](Cl)=[O:36]>C(Cl)Cl.O>[Cl:33][CH2:34][C:35]([NH:1][C:2]1[C:7]2[CH2:8][N:9]([CH:12]([C:14]3[CH:15]=[N:16][C:17]([O:21][CH2:22][C:23]([F:25])([F:26])[F:24])=[C:18]([CH3:20])[CH:19]=3)[CH3:13])[C:10](=[O:11])[C:6]=2[CH:5]=[CH:4][N:3]=1)=[O:36]

Participants

6

Reactant 3

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 89874948HCID 89874948, compound

Product 1

HCID 89874143HCID 89874143, compoundYield 96.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-amino-2-(1-(5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one (230 mg, 0.63 mmol, Example-17, single enantiomer) and pyridine (250 mg, 3.1 mmol) in DCM (5 mL) is added 2-chloroacetyl chloride (89 mg, 0.79 mmol) at rt. The mixture is stirred for 1 hour at rt, and the mixture is diluted with water. The mixture is extracted with DCM. The organic layer is washed with brine, dried over sodium sulfate, and filtered. The filtrate is concentrated. The residue is purified by column chromatography on silica gel eluting with n-hexane/EtOAc (3:1 to 1:1) to give 270 mg (96% yield) of the title compound as pale brown solid.

Workup

  1. extractionThe mixture is extracted with DCM
  2. washThe organic layer is washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated
  6. customThe residue is purified by column chromatography on silica gel eluting with n-hexane/EtOAc (3:1 to 1:1)

Sources & evidence

ORD record
ord-ce74042e23ad493aa7d0543145238211
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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