Water → HCID 178521273, compound

HRID 1403156Notes

Reaction equation

HRID 1403156 reaction equation
Br[CH2:2][C:3]([NH:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([O:12][C:13]2[CH:18]=[C:17]([N:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[N:21]=[C:20]3[CH:28]([F:30])[F:29])[N:16]=[C:15]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)[N:14]=2)[CH2:8][CH2:7]1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH:43]1([NH2:47])[CH2:46][CH2:45][CH2:44]1.O>CN(C)C=O>[CH:43]1([NH:47][CH2:2][C:3]([NH:5][C@H:6]2[CH2:11][CH2:10][C@H:9]([O:12][C:13]3[CH:18]=[C:17]([N:19]4[C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=5[N:21]=[C:20]4[CH:28]([F:30])[F:29])[N:16]=[C:15]([N:31]4[CH2:36][CH2:35][O:34][CH2:33][CH2:32]4)[N:14]=3)[CH2:8][CH2:7]2)=[O:4])[CH2:46][CH2:45][CH2:44]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 75645CyclobutylamineHCID 178520140HCID 178520140, compound

Product 1

HCID 178521273HCID 178521273, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromo-N-[trans-4-({6-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-2-(morpholin-4-yl)pyrimidin-4-yl}oxy)cyclohexyl]acetamide (100 mg) was suspended in dimethylformamide (2 mL), and potassium carbonate (30 mg) and cyclobutylamine (60 μL) were added thereto, followed by stirring at room temperature overnight. To the reaction solution was added water, followed by extraction with ethyl acetate. The extracts were washed with water and saturated brine, the organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by amino silica gel chromatography (hexane:ethyl acetate=40:60-10:90) to obtain N2-cyclobutyl-N-[trans-4-({6-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-2-(morpholin-4-yl)pyrimidin-4-yl}oxy)cyclohexyl]glycinamide (79 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extracts were washed with water and saturated brine
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by amino silica gel chromatography (hexane:ethyl acetate=40:60-10:90)

Sources & evidence

ORD record
ord-aa22c0837e424924be52d1c241b18035
Source dataset
uspto-grants-2014_12
Patent number
US08912180B2

Reaction notes

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