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

반응식

HRID 505717 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
80 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-33fea8cc9f4942c19b0b2108a4cec825
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781428B2

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