Dimethylformamide → HCID 66614711, compound

HRID 473131Notes

Reaction equation

HRID 473131 reaction equation
[F:1][C:2]([F:13])([C:6]1[N:11]=[CH:10][C:9]([F:12])=[CH:8][N:7]=1)[C:3]([O-:5])=O.[Na+].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:39][C:40]1[CH:48]=[CH:47][CH:46]=[CH:45][C:41]=1[C:42]([NH2:44])=[O:43].CN(C=O)C>CCOC(C)=O>[F:13][C:2]([F:1])([C:6]1[N:11]=[CH:10][C:9]([F:12])=[CH:8][N:7]=1)[C:3]([NH:39][C:40]1[CH:48]=[CH:47][CH:46]=[CH:45][C:41]=1[C:42]([NH2:44])=[O:43])=[O:5]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6942AnthranilamideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66608971HCID 66608971, compound

Product 1

HCID 66614711HCID 66614711, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To sodium 2,2-difluoro-2-(5-fluoropyrimidin-2-yl)acetate (400 mg, 1.87 mmol), HATU (850 mg, 2.24 mmol), and 2-aminobenzamide (305 mg, 2.24 mmol) was added DMF (7 mL) and the mixture was stirred at rt overnight. The mixture was diluted with EtOAc and washed with saturated aq NH4Cl, saturated aq NaHCO3, and brine. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 0-12% MeOH/DCM to afford 2-(2,2-difluoro-2-(5-fluoropyrimidin-2-yl)acetamido)benzamide (374 mg, 44%); LC-MS (ESI) m/z 333 (M+Na)+.

Workup

  1. washwashed with saturated aq NH4Cl, saturated aq NaHCO3, and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with 0-12% MeOH/DCM

Sources & evidence

ORD record
ord-c11421964c3341b4b4c45d84021831c0
Source dataset
uspto-grants-2014_01
Patent number
US08633207B2

Reaction notes

Loading…