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Hydrazine, cyclopropyl-, hydrochloride (1:1) → 4-(4-chlorophenyl)-1-cyclopropyl-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-methyl-4,5-dihydropyrrolo-[3,4-c]pyrazol-6(1H)-one

HRID 873951
ノート
印刷プレビュー

反応式

HRID 873951 の反応式
[C:1]([C:4]1[CH:8]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[N:7]([C:16]2[CH:17]=[C:18]([CH3:26])[C:19]3[N:20]([C:22]([CH3:25])=[N:23][N:24]=3)[CH:21]=2)[C:6](=[O:27])[C:5]=1O)(=O)[CH3:2].Cl.[CH:30]1([NH:33][NH2:34])[CH2:32][CH2:31]1>CCO.C1(C)C=CC=CC=1>[Cl:15][C:12]1[CH:11]=[CH:10][C:9]([CH:8]2[C:4]3[C:1]([CH3:2])=[N:34][N:33]([CH:30]4[CH2:32][CH2:31]4)[C:5]=3[C:6](=[O:27])[N:7]2[C:16]2[CH:17]=[C:18]([CH3:26])[C:19]3[N:20]([C:22]([CH3:25])=[N:23][N:24]=3)[CH:21]=2)=[CH:14][CH:13]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 19594967Hydrazine, cyclopropyl-, hydrochloride (1:1)HCID 1177026714-acetyl-5-(4-chlorophenyl)-1-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-hydroxy-1H-pyrrol-2(5H)-one

生成物 1

HCID 862933504-(4-chlorophenyl)-1-cyclopropyl-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-methyl-4,5-dihydropyrrolo-[3,4-c]pyrazol-6(1H)-one収率 59.9%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒
HCID 1140
Toluene
溶媒

実験手順

A mixture of 4-acetyl-5-(4-chlorophenyl)-1-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-hydroxy-1H-pyrrol-2(5H)-one (Step 92.1) (630 mg, 1.588 mmol) and cyclopropylhydrazine hydrochloride (517 mg, 4.76 mmol) in EtOH (8 mL) and toluene (8 mL) was stirred for 2 hr at reflux. The reaction mixture was concentrated, diluted with CH2Cl2/saturated aq. NaHCO3 solution, and extracted with CH2Cl2. The combined organic layers were washed with water and brine, dried over Na2SO4 and evaporated. The crude material was purified by silica gel column chromatography (1% ammonia/5% MeOH/CH2Cl2) to afford the title product (412 mg, 0.952 mmol, 59.9% yield) as a yellow foam. tR: 0.95 min (LC-MS 2); ESI-MS: 433 [M+H]+ (LC-MS 2); Rf=0.28 (1% ammonia/5% MeOH/CH2Cl2); 1H NMR (400 MHz, DMSO-d6) δ ppm 0.98-1.11 (m, 2H) 1.18-1.29 (m, 2H) 1.92 (s, 3H) 2.43 (s, 3H) 2.61 (s, 3H) 3.75-3.87 (m, 1H) 6.41 (s, 1H) 7.27-7.39 (m, 5H) 8.33-8.48 (m, 1H).

後処理

  1. temperatureat reflux
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with CH2Cl2/saturated aq. NaHCO3 solution
  4. extractionextracted with CH2Cl2
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customThe crude material was purified by silica gel column chromatography (1% ammonia/5% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-65cd1ee6f6d646d39835dec548bcd0dc
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08975417B2

反応ノート

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