Potassium Hydroxide → HCID 59587454, compound

HRID 389751Notes

Reaction equation

HRID 389751 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]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])=[C:12]([C:14]#[N:15])[N:13]=1.[OH-:25].[K+]>O>[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[C:9]1[O:10][C:11]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])=[C:12]([C:14]([NH2:15])=[O:25])[N:13]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 68521713HCID 68521713, compound

Product 1

HCID 59587454HCID 59587454, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

To a suspension of 2-(2,6-difluorophenyl)-5-(2-methoxyphenylamino)oxazole-4-carbonitrile (0.018 g, 0.055 mmol, prepared according to the procedure described for Q-1 step a) in water (4.5 mL) was added 1M aqueous potassium hydroxide (0.27 mL, 0.27 mmol) and the resulting mixture stirred at 140° C. in the microwave for 15 minutes. The solvent was removed in vacuo and the residue purified by preparative HPLC to afford 2-(2,6-difluorophenyl)-5-(2-methoxyphenylamino)oxazole-4-carboxamide (0.0104 g, 0.030 mmol, 55%). 1H NMR (DMSO) δ 3.92 (3H, s), 6.99 (1H, ddd), 7.04 (1H, ddd), 7.12 (1H, dd), 7.35 (2H, t), 7.42 (2H, br. s), 7.64 (1H, m), 7.68 (1H, dd), 9.48 (1H, s). LCMS (2) Rt: 2.86 min; m/z (ES+) 346.

Workup

  1. customprepared
  2. customThe solvent was removed in vacuo
  3. customthe residue purified by preparative HPLC

Sources & evidence

ORD record
ord-be4647370bdf4d7ca4cb2a9035d0f672
Source dataset
uspto-grants-2013_02
Patent number
US08378095B2

Reaction notes

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