Potassium Carbonate → HCID 178502270, compound

HRID 1403134Notes

Reaction equation

HRID 1403134 reaction equation
Cl[C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]([N:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[N:12]=[C:11]2[CH:19]([F:21])[F:20])[CH:3]=1.Cl.C[N:24]([C@@H:28]1[CH2:32][CH2:31][N:30]([C@H:33]2[CH2:38][CH2:37][C@H:36]([NH2:39])[CH2:35][CH2:34]2)[C:29]1=[O:40])[C:25](=[O:27])[OH:26].[C:41](=O)([O-])[O-].[K+].[K+].C(N(C(C)C)C(C)C)C>C(OCC)(=O)C.O.CN(C)C(=O)C>[CH3:41][O:26][C:25](=[O:27])[NH:24][C@@H:28]1[CH2:32][CH2:31][N:30]([C@H:33]2[CH2:38][CH2:37][C@H:36]([NH:39][C:2]3[CH:3]=[C:4]([N:10]4[C:14]5[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=5[N:12]=[C:11]4[CH:19]([F:21])[F:20])[N:5]=[C:6]([S:8][CH3:9])[N:7]=3)[CH2:35][CH2:34]2)[C:29]1=[O:40]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 86667188HCID 86667188, compoundHCID 178486069HCID 178486069, compound

Product 1

HCID 178502270HCID 178502270, compoundYield 76.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-[6-chloro-2-(methylsulfanyl)pyrimidin-4-yl]-2-(difluoromethyl)-1H-benzimidazole (350 mg), methyl[(3R)-1-(trans-4-aminocyclohexyl)-2-oxopyrrolidin-3-yl]carbamate hydrochloride (344 mg), potassium carbonate (178 mg), N-ethyl-N-isopropylpropan-2-amine (1.1 mL), and N,N-dimethylacetamide (1.75 mL) was stirred at 60° C. overnight. To the reaction solution were added water and ethyl acetate. The insoluble matter was collected by filtration, followed by extraction with ethyl acetate. The solvent was evaporated under reduced pressure, and then the residue and the insoluble matter were combined. Ethyl acetate was added thereto, and the mixture was suspended, stirred, and then collected by filtration. The resultant was washed with water and dried to obtain methyl{(3R)-1-[trans-4-({6-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-2-(methylsulfanyl)pyrimidin-4-yl}amino)cyclohexyl]-2-oxopyrrolidin-3-yl}carbamate (446 mg).

Workup

  1. filtrationThe insoluble matter was collected by filtration
  2. extractionfollowed by extraction with ethyl acetate
  3. customThe solvent was evaporated under reduced pressure
  4. additionEthyl acetate was added
  5. stirringstirred
  6. filtrationcollected by filtration
  7. washThe resultant was washed with water
  8. customdried

Sources & evidence

ORD record
ord-995584a83eca4640976ab139face2554
Source dataset
uspto-grants-2014_12
Patent number
US08912180B2

Reaction notes

Loading…