Sodium Hydroxide → 5-(4-((Piperidin-4-ylmethyl)carbamoyl)phenylamino)-2-(2,6-difluorophenyl)oxazole-4-carboxamide

HRID 389758Notes

Reaction equation

HRID 389758 reaction equation
[C:1]([C:3]1[N:4]=[C:5]([C:32]2[C:37]([F:38])=[CH:36][CH:35]=[CH:34][C:33]=2[F:39])[O:6][C:7]=1[NH:8][C:9]1[CH:31]=[CH:30][C:12]([C:13]([NH:15][CH2:16][CH:17]2[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]2)=[O:14])=[CH:11][CH:10]=1)#[N:2].C(=O)(O)[O-:41].[Na+].[OH-].[Na+]>S(=O)(=O)(O)O>[NH:20]1[CH2:19][CH2:18][CH:17]([CH2:16][NH:15][C:13]([C:12]2[CH:30]=[CH:31][C:9]([NH:8][C:7]3[O:6][C:5]([C:32]4[C:37]([F:38])=[CH:36][CH:35]=[CH:34][C:33]=4[F:39])=[N:4][C:3]=3[C:1]([NH2:2])=[O:41])=[CH:10][CH:11]=2)=[O:14])[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 59587428Tert-butyl 4-((4-(4-cyano-2-(2,6-difluorophenyl)oxazol-5-ylamino)benzamido)methyl)piperidine-1-carboxylate

Product 1

HCID 595875095-(4-((Piperidin-4-ylmethyl)carbamoyl)phenylamino)-2-(2,6-difluorophenyl)oxazole-4-carboxamideYield 14%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of tert-butyl 4-((4-(4-cyano-2-(2,6-difluorophenyl)oxazol-5-ylamino)benzamido)methyl)piperidine-1-carboxylate (0.028 g, 0.052 mmol) in concentrated sulfuric acid (1 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 then basified to pH14 with 5M NaOH and extracted with EtOAc. The combined organic phases were dried over MgSO4 and the solvent removed in vacuo to afford 5-(4-((piperidin-4-ylmethyl)carbamoyl)phenylamino)-2-(2,6-difluorophenyl)oxazole-4-carboxamide (0.003 g, 0.007 mmol, 14%) as a yellow solid. 1H NMR (CD3OD) δ 1.51 (2H, m), 2.00 (3H, m), 2.99 (2H, t), 3.35 (2H, m), 3.45 (2H, m), 7.22 (2H, t), 7.53 (2H, d), 7.60 (1H, m), 7.87 (2H, d), 8.55 (1H, br s). LCMS (2) Rt: 1.85 min; m/z (ES+) 456.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-66cca6df1df0457abac1c235a0548ca3
Source dataset
uspto-grants-2013_02
Patent number
US08378095B2

Reaction notes

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