Potassium Carbonate → HCID 66757683, compound

HRID 1643321Notes

Reaction equation

HRID 1643321 reaction equation
[NH2:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([NH:8][C:9]2[CH:14]=[C:13]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)[CH:12]=[CH:11][C:10]=2[NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:7])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:37][C:38]([NH:40][CH3:41])=[O:39]>CC#N.CCOC(C)=O>[NH2:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([NH:8][C:9]2[CH:14]=[C:13]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)[CH:12]=[CH:11][C:10]=2[N:20]([CH2:37][C:38]([NH:40][CH3:41])=[O:39])[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:24])[CH3:25])=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 667732-chloro-N-methylacetamideHCID 57857127HCID 57857127, compound

Product 1

HCID 66757683HCID 66757683, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl [2-[(4-aminobenzoyl)amino]-4-(2-thienyl)phenyl]carbamate (mg, mmol) in CH3CN was added K2CO3 and 2-chloro-N-methylacetamide. The reaction was allowed to stir at reflux overnight. The crude reaction mixture was diluted with EtOAc (20 mL) and then washed with sat.'d aq. NaHCO3 (1×10 mL). The organic layer was dried over MgSO4, filtered, concentrated in vacuo. The crude residue was purified by reverse-phase chromatography (10-100% MeCN/H2O with 0.05% TFA). The appropriate fractions were combined and concentrated in vacuo and gave the desired tert-butyl [2-[(4-aminobenzoyl)amino]-4-(2-thienyl)phenyl][2-(methylamino)-2-oxoethyl]carbamate which was confirmed by MS: cal'd 481.2 (MH+), exp 481.2 (MH+).

Workup

  1. temperatureat reflux overnight
  2. customThe crude reaction mixture
  3. washwashed with sat.'d aq. NaHCO3 (1×10 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by reverse-phase chromatography (10-100% MeCN/H2O with 0.05% TFA)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2bac197bba4d4e9587fdd07084226f61
Source dataset
uspto-grants-2012_02
Patent number
US08119685B2

Reaction notes

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