Methyl Isocyanate → HCID 46205893, compound

HRID 389720Notes

Reaction equation

HRID 389720 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-d8f3a35f24374a90b6d0a109f6971977
Source dataset
uspto-grants-2013_02
Patent number
US08378095B2

Reaction notes

Loading…