Trifluoroacetic acid → N-(4-Chloro-3-(1-(3,4-di chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-2-fluorobenzyl)pivalamide

HRID 59497노트

반응식

HRID 59497 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][NH:10]C(OC(C)(C)C)=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[Cl:18][C:19]1[C:24]([C:25]([N:27]=[C:28]=[O:29])=O)=[C:23]([F:30])[C:22]([CH2:31][NH:32][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:21][CH:20]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:31][NH:32][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])=[C:23]([F:30])[C:24]=1[C:25]1[NH:27][C:28](=[O:29])[N:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[N:10]=1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 900197456-Chloro-2-fluoro-3-(pivalamidomethyl)benzoyl isocyanateHCID 90065722Tert-butyl 2-(3,4-dichlorophenyl)hydrazinecarboxylate

생성물 1

HCID 136246000N-(4-Chloro-3-(1-(3,4-di chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-2-fluorobenzyl)pivalamide수율 7.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of tert-butyl 2-(3,4-dichlorophenyl)hydrazinecarboxylate (Intermediate-52, 0.060 g, 0.21 mmol) in DCM (10 mL) was added solution of 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoyl isocyanate (Intermediate-51, 0.101 g, 0.32 mmol) in DCM and the reaction mixture was stirred for 20 h at room temperature, followed by addition of TFA (3 mL) and further stirred for 20 h at room temperature. The reaction mass was quenched in water, extracted with DCM and concentrated to afford crude product which was purified by column chromatography eluting with MeOH:DCM to afford 0.007 g of pure product. 1H NMR (300 MHz, CDCl3): δ 1.20 (s, 9H), 4.44 (d, J=5.4 Hz, 2H), 6.20 (m, 1H), 7.29 (m, 1H), 7.41-7.49 (m, 2H), 7.91 (d, J=8.1 Hz, 1H), 8.15 (s, 1H); MS (m/z): 471.26 (M+).

후처리

  1. stirringfurther stirred for 20 h at room temperature
  2. customThe reaction mass was quenched in water
  3. extractionextracted with DCM
  4. concentrationconcentrated
  5. customto afford crude product which
  6. customwas purified by column chromatography
  7. washeluting with MeOH

출처 및 근거

ORD 기록
ord-f11726a7fafc4496a0c0f2ef81705018
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09439890B2

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