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

HRID 1410487노트

반응식

HRID 1410487 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-87350d95464d4423971f856ff4752030
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921544B2

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