Sodium Bicarbonate → 2-(2,6-Difluorophenyl)-5-(4-morpholinophenylamino)oxazole-4-carboxamide

HRID 714983Notes

Reaction equation

HRID 714983 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][C:20]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)=[CH:19][CH:18]=2)=[C:12]([C:14]#[N:15])[N:13]=1.C(=O)(O)[O-:30].[Na+]>S(=O)(=O)(O)O>[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:18]=[CH:19][C:20]([N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)=[CH:21][CH:22]=2)=[C:12]([C:14]([NH2:15])=[O:30])[N:13]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 59587453HCID 59587453, compound

Product 1

HCID 595876272-(2,6-Difluorophenyl)-5-(4-morpholinophenylamino)oxazole-4-carboxamideYield 85%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 2-(2,6-difluorophenyl)-5-(4-morpholinophenylamino)oxazole-4-carbonitrile (0.035 g, 0.09 mmol) in concentrated sulfuric acid (1.7 mL) was stirred at room temperature for 1.5 hours. The solution was neutralised by pouring into saturated sodium bicarbonate solution. The aqueous phase was extracted with EtOAc. The combined organic phase was dried over MgSO4 and the solvent removed in vacuo to afford 2-(2,6-difluorophenyl)-5-(4-morpholinophenylamino)oxazole-4-carboxamide (0.031 g, 0.077 mmol, 85%) as a yellow solid. 1H NMR (DMSO) δ 3.06 (4H, t), 3.73 (4H, t), 6.94 (2H, d), 7.28 (2H, br. s), 7.32 (4H, m), 7.62 (1H, m), 9.13 (1H, s). LCMS (2) Rt: 2.60 min; m/z (ES+) 401.

Workup

  1. extractionThe aqueous phase was extracted with EtOAc
  2. dry with materialThe combined organic phase was dried over MgSO4
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-90e74ce3b9f84b25951756bc86596e23
Source dataset
uspto-grants-2015_11
Patent number
US09187465B2

Reaction notes

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