Methyl Isocyanate → HCID 46205893, compound

HRID 714953Notes

Reaction equation

HRID 714953 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-a56f7dbb6070415a98f681a3f733199b
Source dataset
uspto-grants-2015_11
Patent number
US09187465B2

Reaction notes

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