2-Chloro-4-hydrazinylbenzonitrile hydrochloride → methyl 2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylate

HRID 505717

反応式

HRID 505717 の反応式
[CH:1]1([CH:6]=[C:7]2[CH2:16][CH2:15][C:14]3[CH:13]=[C:12]([C:17]([O:19][CH3:20])=[O:18])[CH:11]=[CH:10][C:9]=3[C:8]2=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[Cl:23][C:24]1[CH:31]=[C:30]([NH:32][NH2:33])[CH:29]=[CH:28][C:25]=1[C:26]#[N:27]>C(O)C>[Cl:23][C:24]1[CH:31]=[C:30]([N:32]2[CH:6]([CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:7]3[C:8]([C:9]4[CH:10]=[CH:11][C:12]([C:17]([O:19][CH3:20])=[O:18])=[CH:13][C:14]=4[CH2:15][CH2:16]3)=[N:33]2)[CH:29]=[CH:28][C:25]=1[C:26]#[N:27]

参加物

4

反応物 2

HCID 221118492-Chloro-4-hydrazinylbenzonitrile hydrochlorideHCID 66722547Methyl 6-(cyclopentylmethylene)-5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate

生成物 1

HCID 24983916methyl 2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylate収率 87.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
80 °C

実験手順

Methyl 6-(cyclopentylmethylene)-5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate (Preparation 18, 2.8 g, 9.9 mmol) was suspended in ethanol (100 mL) and 2-chloro-4-hydrazinylbenzonitrile hydrochloride (Preparation 1, 2.6 g, 12.8 mmol) was added. The solution was heated to 80° C. for eight hours. The solution was returned to ambient temperature. The resulting solid was collected by vacuum filtration and washed with cold ethanol to provide the title compound largely present as (±)-(3SR,3aRS)-methyl 2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylate (3.75 g, 87% yield). LC/MS on 4.6×50 mm C-18 column, tR=7.45 minutes (10 to 90% acetonitrile/water over 8 minutes at 2 mL/minute with detection 254 nm, at 50° C.); ES-MS m/z 434 (M+H); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.06-1.54 (m, 6H), 1.62-1.74 (m, 1H), 1.73-1.87 (m, 1H), 1.99-2.09 (m, 1H), 2.21 (dd, J=7.79, 2.15 Hz, 1H), 2.82-2.94 (m, 2H), 3.09 (d, J=16.92 Hz, 1H), 3.54-3.66 (m, 1H), 3.84 (s, 3H), 4.95 (dd, J=9.67, 5.64 Hz, 1H), 7.19 (dd, J=9.26, 1.75 Hz, 1H), 7.39 (d, J=2.15 Hz, 1H), 7.67 (d, J=8.86 Hz, 1H), 7.82 (d, J=8.32 Hz, 1H), 7.86 (s, 1H), 8.10 (d, J=8.06 Hz, 1H).

後処理

  1. customwas returned to ambient temperature
  2. filtrationThe resulting solid was collected by vacuum filtration
  3. washwashed with cold ethanol

出典と根拠

ORDレコード
ord-33fea8cc9f4942c19b0b2108a4cec825
出典データセット
uspto-grants-2010_08
特許番号
US07781428B2

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