Ammonium Chloride → 3-Tert-butyl-isoxazole-5-carboxylic acid [3-amino-4-chloro-6-(2-trifluoromethyl-phenyl)-pyridin-2-yl]-amide

HRID 570213노트

반응식

HRID 570213 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]([F:17])([F:16])[F:15])[N:5]=[C:4]([NH:18][C:19]([C:21]2[O:25][N:24]=[C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:22]=2)=[O:20])[C:3]=1[N+:30]([O-])=O.[Cl-].[NH4+]>CCO.O.[Fe]>[NH2:30][C:3]1[C:4]([NH:18][C:19]([C:21]2[O:25][N:24]=[C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:22]=2)=[O:20])=[N:5][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]([F:15])([F:16])[F:17])=[CH:7][C:2]=1[Cl:1]

참가 물질

6

반응물 2

HCID 25517Ammonium ChlorideHCID 674109013-Tert-butyl-isoxazole-5-carboxylic acid [4-chloro-3-nitro-6-(2-trifluoromethyl-phenyl)-pyridin-2-yl]-amide

생성물 1

HCID 674111003-Tert-butyl-isoxazole-5-carboxylic acid [3-amino-4-chloro-6-(2-trifluoromethyl-phenyl)-pyridin-2-yl]-amide

시약·촉매·용매 3

HCID 23925Iron촉매HCID 702Ethanol용매HCID 962Water용매

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온도
50 °C

실험 절차

A solution of 3-tert-butyl-isoxazole-5-carboxylic acid [4-chloro-3-nitro-6-(2-trifluoromethyl-phenyl)-pyridin-2-yl]-amide (40.7 mg, 0.0868 mmol, prepared as described in STEP A above) in EtOH (5 mL) and water (2.5 mL) was treated with ammonium chloride (46.4 mg, 0.868 mmol) and iron powder (24.2 mg, 0.434 mmol), and the mixture was stirred at 50° C. for 3 h. The cooled mixture was concentrated in vacuo and partitioned between EtOAc (25 mL) and water (20 mL). The aqueous layer was extracted with EtOAc (20 mL). The combined organic extracts were dried over MgSO4 and concentrated in vacuo. The residue was purified on a 12-g SEPRA Si 50 SPE column (Flow rate=20 mL/min; Eluent=EtOAc-hexanes, 1:99 for 10 min, then 1:99 to 1:3 over 40 min) to yield 3-tert-butyl-isoxazole-5-carboxylic acid [3-amino-4-chloro-6-(2-trifluoromethyl-phenyl)-pyridin-2-yl]-amide as a yellow solid. Mass Spectrum (LCMS, ESI pos.): Calculated for C21H18N4O2ClF3: 439.1 (M+H); Measured: 439.1.

후처리

  1. concentrationThe cooled mixture was concentrated in vacuo
  2. custompartitioned between EtOAc (25 mL) and water (20 mL)
  3. extractionThe aqueous layer was extracted with EtOAc (20 mL)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified on a 12-g SEPRA Si 50 SPE column (Flow rate=20 mL/min
  7. waitEluent=EtOAc-hexanes, 1:99 for 10 min

출처 및 근거

ORD 기록
ord-dc173ed1d46049469d34062d15ec68ed
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09023846B2

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