4-Methoxyphenylhydrazine hydrochloride → 1-[4-Methoxyphenyl]-3-trifluoromethyl-6-[4-iodophenyl]-1,4,5,6-tetrahydropyrazolo-[3,4-c]-pyridin-7-one

HRID 497428노트

반응식

HRID 497428 반응식
[I:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C:14](=O)[C:15]([F:18])([F:17])[F:16])[C:10](=O)[C:9]2=[O:21])=[CH:4][CH:3]=1.Cl.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([NH:31][NH2:32])=[CH:27][CH:26]=1>Cl.CO>[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]2[C:10]3[C:9](=[O:21])[N:8]([C:5]4[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=4)[CH2:13][CH2:12][C:11]=3[C:14]([C:15]([F:18])([F:17])[F:16])=[N:32]2)=[CH:27][CH:26]=1

참가 물질

5

반응물 2

HCID 27239044-Methoxyphenylhydrazine hydrochlorideHCID 222404772,3-Piperidinedione, 1-(4-iodophenyl)-4-(2,2,2-trifluoroacetyl)-

생성물 1

HCID 223185911-[4-Methoxyphenyl]-3-trifluoromethyl-6-[4-iodophenyl]-1,4,5,6-tetrahydropyrazolo-[3,4-c]-pyridin-7-one수율 74%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 887Methanol용매

실험 절차

1-(4-iodophenyl)-4-(trifluoroacetyl)-2,3-piperidinedione from Part C (10.0 g, 24.3 mmol) and 4-methoxyphenylhydrazine hydrochloride (4.28 g, 24.3 mmol) were dissolved in HCl (1N, 200 mL) and methanol (400 mL). The mixture was refluxed overnight. The reaction mixture was cooled to room temperature and quenched with water. It was extracted with ethyl acetate, washed with brine, and dried (Na2SO4). Purification by silica gel chromatography using 0%-100% ethyl acetate/hexane gradient as eluent afforded the desired pyrazole 9.28 g (74%). 1HNMR (CDCl3) δ 7.69 (d, 2H), 7.45 (d, 2H), 7.06 (d, 2H), 6.92 (d, 2H), 4.11 (t, 2H), 3.81 (s, 3H), 3.15 (t, 2H) ppm; Mass Spec (M+H)+514.3.

후처리

  1. temperatureThe mixture was refluxed overnight
  2. customquenched with water
  3. extractionIt was extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. customPurification by silica gel chromatography

출처 및 근거

ORD 기록
ord-3d7aae0ca5c74524ac35372144a16d2a
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06949550B2

반응 노트

불러오는 중…