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

HRID 497428ノート

反応式

HRID 497428 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3d7aae0ca5c74524ac35372144a16d2a
出典データセット
uspto-grants-2005_09
特許番号
US06949550B2

反応ノート

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