Potassium Carbonate → HCID 178502271, compound

HRID 1403165Notes

Reaction equation

HRID 1403165 reaction equation
[F:1][CH:2]([F:28])[C:3]1[N:7]([C:8]2[CH:13]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:11]=[C:10](S(C)(=O)=O)[N:9]=2)[C:6]2[CH:24]=[CH:25][CH:26]=[CH:27][C:5]=2[N:4]=1.Cl.C[N:31]([C@H:35]1[CH2:39][CH2:38][N:37]([C@H:40]2[CH2:45][CH2:44][C@H:43]([NH2:46])[CH2:42][CH2:41]2)[C:36]1=[O:47])[C:32](=[O:34])[OH:33].[C:48](=O)([O-])[O-].[K+].[K+].CN(C)C(=O)C>O>[CH3:48][O:33][C:32](=[O:34])[NH:31][C@H:35]1[CH2:39][CH2:38][N:37]([C@H:40]2[CH2:45][CH2:44][C@H:43]([NH:46][C:10]3[N:9]=[C:8]([N:7]4[C:6]5[CH:24]=[CH:25][CH:26]=[CH:27][C:5]=5[N:4]=[C:3]4[CH:2]([F:28])[F:1])[CH:13]=[C:12]([N:14]4[CH2:19][CH2:18][O:17][CH2:16][CH2:15]4)[N:11]=3)[CH2:42][CH2:41]2)[C:36]1=[O:47]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 67980988HCID 67980988, compoundHCID 178486070HCID 178486070, compound

Product 1

HCID 178502271HCID 178502271, compoundYield 35.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-(difluoromethyl)-1-[2-(methylsulfonyl)-6-(morpholin-4-yl)pyrimidin-4-yl]-1H-benzimidazole (200 mg) and methyl[(3S)-1-(trans-4-aminocyclohexyl)-2-oxopyrrolidin-3-yl]carbamate hydrochloride (214 mg), potassium carbonate (135 mg), N-ethyl-N-diisopropylpropan-2-amine (0.38 mL) and N,N-dimethylacetamide (3 mL) was stirred at 100° C. for 6 hours. After leaving to be cooled, to the reaction solution was added water, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The desiccant was removed by filtration and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol-100:0-80:20) to obtain methyl{(3S)-1-[trans-4-({4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(morpholin-4-yl)pyrimidin-2-yl}amino)cyclohexyl]-2-oxopyrrolidin-3-yl}carbamate (102 mg) as a white powder.

Workup

  1. customAfter leaving
  2. temperatureto be cooled, to the reaction solution
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe desiccant was removed by filtration
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (chloroform/methanol-100:0-80:20)

Sources & evidence

ORD record
ord-2dc0aefda2bd4392909982d7b01adb00
Source dataset
uspto-grants-2014_12
Patent number
US08912180B2

Reaction notes

Loading…