Methyl Isocyanate → HCID 46205893, compound

HRID 1410452Notes

Reaction equation

HRID 1410452 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[O:10][C:11]([C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)=[CH:19][CH:18]=2)=[C:12]([C:14]([NH2:16])=[O:15])[N:13]=1.[CH3:29][N:30]=[C:31]=[O:32]>C(Cl)Cl>[C:14]([C:12]1[N:13]=[C:9]([C:3]2[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[O:10][C:11]=1[C:17]1[CH:18]=[CH:19][C:20]([N:23]2[CH2:24][CH2:25][N:26]([C:31]([NH:30][CH3:29])=[O:32])[CH2:27][CH2:28]2)=[CH:21][CH:22]=1)(=[O:15])[NH2:16]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 59587408HCID 59587408, compound

Product 1

HCID 46205893HCID 46205893, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-(2,6-difluorophenyl)-5-(4-(piperazin-1-yl)phenyl)oxazole-4-carboxamide (0.029 g, 0.075 mmol) in DCM (3 mL) was added methyl isocyanate (8 uL, 0.136 mmol). The resulting solution was stirred at room temperature overnight. The solvent was removed in vacuo to afford 4-(4-(4-carbamoyl-2-(2,6-difluorophenyl)oxazol-5-yl)phenyl)-N-methylpiperazine-1-carboxamide (0.026 g, 0.059 mmol, 79%) as a yellow solid. 1H NMR (DMSO) 2.85 (3H, d), 3.34 (4H, m), 3.56 (4H, m), 4.46 (1H, br. q), 5.49 (1H, br. s), 6.95 (2H, d), 7.07 (2H, t), 7.20 (1H, br. s), 7.46 (1H, m), 8.32 (2H, d). LCMS (2) Rt: 2.43 min; m/z (ES+) 442.

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-c61f45df14164f8185820bf0dd82fe63
Source dataset
uspto-grants-2014_12
Patent number
US08921544B2

Reaction notes

Loading…