Diisopropylamine → HCID 76765796, 화합물

HRID 69398노트

반응식

HRID 69398 반응식
[CH2:1]([NH:5][C:6](=[O:31])[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH2:17][C:16]([C:22]3[CH:27]=[C:26]([Cl:28])[CH:25]=[C:24]([Cl:29])[CH:23]=3)([C:18]([F:21])([F:20])[F:19])[O:15][N:14]=2)=[CH:9][C:8]=1[CH3:30])[CH2:2][CH2:3][CH3:4].C(NC(C)C)(C)C.C([Li])CCC>O1CCCC1>[CH2:1]([NH:5][C:6](=[O:31])[C:7]1[CH:12]=[CH:11][C:10]([C:13](=[N:14][OH:15])[CH:17]=[C:16]([C:22]2[CH:27]=[C:26]([Cl:28])[CH:25]=[C:24]([Cl:29])[CH:23]=2)[C:18]([F:19])([F:21])[F:20])=[CH:9][C:8]=1[CH3:30])[CH2:2][CH2:3][CH3:4]

참가 물질

5

반응물 3

HCID 7912DiisopropylamineHCID 67295194HCID 67295194, 화합물HCID 178418339Butyllithium

생성물 1

HCID 76765796HCID 76765796, 화합물수율 70%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of N-butyl-4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzamide (made as described in EP 1,731,512) (1670 mg, 4.13 mmol) and N,N-diisopropylamine (880 mg, 8.69 mmol) in dry tetrahydrofuran (10 ml) was added n-butyl lithium (“n-BuLi”) (1.55M in hexane) (5.6 ml, 8.69 mmol) at −90° C. The reaction mixture was allowed to warm to 0° C. over a period of 2 hours and quenched by addition of aqueous ammonium chloride (saturated). The mixture was extracted several times with diethyl ether. The combined organic extracts were dried over magnesium sulfate and concentrated. The residue was purified by chromatography on silica gel (eluent: hexane/ethyl acetate 2:1) to give N-butyl-4-[3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-1-hydroxyimino-but-2-enyl]-2-methyl-benzamide (1180 mg, 70% yield) as a yellow resin. 1H-NMR (CDCl3, 300 MHz): 8.52 (bs, 1H), 7.45-7.36 (m, 6H), 6.75 (s, 1H), 5.81 (m, 1H), 3.46-3.43 (m, 2H), 2.47 (s, 3H), 1.54-1.39 (m, 4H), 0.97 (t, 3H) ppm.

후처리

  1. customquenched by addition of aqueous ammonium chloride (saturated)
  2. extractionThe mixture was extracted several times with diethyl ether
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel (eluent: hexane/ethyl acetate 2:1)

출처 및 근거

ORD 기록
ord-e244720a0e774435a15b3bc3d2ca2a8c
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822502B2

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