Methylamine → HCID 71061660, compound

HRID 2201848Notes

Reaction equation

HRID 2201848 reaction equation
Br[CH2:2][C:3]1[CH:25]=[C:24]([Cl:26])[C:6]([C:7]([C:9]2[C:17]3[C:12](=[C:13]([NH:18][C:19]([CH:21]4[CH2:23][CH2:22]4)=[O:20])[N:14]=[CH:15][CH:16]=3)[NH:11][CH:10]=2)=[O:8])=[C:5]([Cl:27])[CH:4]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:34][NH2:35]>C(#N)C.O>[Cl:27][C:5]1[CH:4]=[C:3]([CH2:2][NH:35][CH3:34])[CH:25]=[C:24]([Cl:26])[C:6]=1[C:7]([C:9]1[C:17]2[C:12](=[C:13]([NH:18][C:19]([CH:21]3[CH2:22][CH2:23]3)=[O:20])[N:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1)=[O:8]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 10796Cesium carbonateHCID 86720652HCID 86720652, compound

Product 1

HCID 71061660HCID 71061660, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of N-{3-[4-(bromomethyl)-2,6-dichlorobenzoyl]-1H-pyrrolo[2,3-c]pyridin-7-yl}cyclopropanecarboxamide (50 mg, 0.11 mmol) in acetonitrile, cesium carbonate (70 mg, 0.21 mmol) was added and stirred at same temperature. Methyl amine (6.8 mg, 0.21 mmol) was added at 0° C. The reaction mixture was then stirred at room temperature for 3 h. On completion, the reaction mixture was diluted with water and extracted with ethyl acetate, organic layer was separated, washed with brine, dried over sodium sulfate and concentrated under vacuum. Purification by silica gel (100-200) column chromatography using dichloromethane and methanol gradient as eluent afforded N-(3-{2,6-dichloro-4-[(methylamino)methyl]benzoyl}-1H-pyrrolo[2,3-c]pyridin-7-yl)cyclopropanecarboxamide (7.2 mg, 16%).

Workup

  1. stirringThe reaction mixture was then stirred at room temperature for 3 h
  2. extractionextracted with ethyl acetate, organic layer
  3. customwas separated
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customPurification by silica gel (100-200) column chromatography

Sources & evidence

ORD record
ord-9d4f856d43c0414790e1e97f7c49c925
Source dataset
uspto-grants-2016_06
Patent number
US09364466B2

Reaction notes

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