Ethyl Acetate → 2-amino-2-methyl-4-(3-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butan-1-ol

HRID 1506403노트

반응식

HRID 1506403 반응식
[NH2:1][C:2]([CH3:38])([CH2:8][CH2:9][C:10]1[CH:11]=[C:12]2[C:35](=[CH:36][CH:37]=1)[C:16]1=[N:17][O:18][C:19]([C:20]3[CH:21]=[N:22][N:23]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C:24]=3[C:25]([F:28])([F:27])[F:26])=[C:15]1[CH2:14][CH2:13]2)[C:3](OCC)=[O:4].[BH4-].[Na+].C(OCC)(=O)C.[Cl-].[NH4+]>C(O)C.O>[NH2:1][C:2]([CH3:38])([CH2:8][CH2:9][C:10]1[CH:11]=[C:12]2[C:35](=[CH:36][CH:37]=1)[C:16]1=[N:17][O:18][C:19]([C:20]3[CH:21]=[N:22][N:23]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:24]=3[C:25]([F:28])([F:27])[F:26])=[C:15]1[CH2:14][CH2:13]2)[CH2:3][OH:4]

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 67170053ethyl 2-amino-2-methyl-4-(3-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butanoate

생성물 1

HCID 671710162-amino-2-methyl-4-(3-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butan-1-ol수율 43.5%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

To a stirred solution of ethyl 2-amino-2-methyl-4-(3-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butanoate (Preparation 50D, 80 mg, 0.153 mmol) in ethanol (1 mL) was added sodium borohydride (30 mg, 0.793 mmol) at room temperature. The reaction mixture was stirred at room temperature for 19 hr before ethyl acetate (4 mL) and water (2 ml) were added followed by the addition of saturated aqueous ammonium chloride solution (3 mL). The aqueous layer was separated and extracted with ethyl acetate (3×2 mL). The combined ethyl acetate solutions were dried over sodium sulfate and concentrated under reduced pressure to give a white solid. The solid was triturated with ethyl acetate to give 2-amino-2-methyl-4-(3-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butan-1-ol (32 mg, 0.066 mmol, 43.5% yield) as a white solid.

후처리

  1. additionwere added
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate (3×2 mL)
  4. dry with materialThe combined ethyl acetate solutions were dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a white solid
  7. customThe solid was triturated with ethyl acetate

출처 및 근거

ORD 기록
ord-73f227cf91e14b4e91f32643b5996ab3
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216972B2

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