2-Bromo-6-phenylcyclohexanone → 2-(4-Methyl-imidazol-1-yl)-5-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-ylamino)-benzonitrile

HRID 2076013노트

반응식

HRID 2076013 반응식
[C:1]([C:3]1[CH:4]=[C:5]([NH:15][C:16]([NH2:18])=[S:17])[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1)#[N:2].Br[CH:20]1[CH2:25][CH2:24][CH2:23][CH:22]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:21]1=O>C(O)C>[CH3:14][C:12]1[N:11]=[CH:10][N:9]([C:8]2[CH:7]=[CH:6][C:5]([NH:15][C:16]3[S:17][C:28]4[CH2:29][CH2:30][CH2:31][CH:26]([C:22]5[CH:23]=[CH:24][CH:25]=[CH:20][CH:21]=5)[C:27]=4[N:18]=3)=[CH:4][C:3]=2[C:1]#[N:2])[CH:13]=1

참가 물질

4

반응물 2

HCID 127791292-Bromo-6-phenylcyclohexanoneHCID 86624673[3-Cyano-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea

생성물 1

HCID 441951862-(4-Methyl-imidazol-1-yl)-5-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-ylamino)-benzonitrile수율 88%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A suspension of [3-cyano-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea (64.3 mg, 0.25 mmol) and of 2-bromo-6-phenyl-cyclohexanone (63.3 mg, 0.25 mmol) in ethanol (2 mL) was heated to reflux under an atmosphere of nitrogen for 2 days. After cooling to room temperature the solvent was evaporated under reduced pressure. The residue was suspended in dichloromethane/diethyl ether. The precipitated solid was filtered off, washed with diethyl ether and dried under reduced pressure to yield the title compound (90 mg, 88%) as a pale-brown solid. MS ISP (m/e): 412.2 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=10.75 (s, 1H), 9.31 (s, 1H), 8.16 (s, 1H), 7.78 (m, 2H), 7.65 (d, 1H), 7.30 (t, 2H), 7.17 (m, 3H), 4.08 (m, 1H), 2.75 (m, 2H), 2.34 (s, 3H), 2.15 m, 2H), 1.76 (m, 2H).

후처리

  1. temperatureto reflux under an atmosphere of nitrogen for 2 days
  2. customwas evaporated under reduced pressure
  3. filtrationThe precipitated solid was filtered off
  4. washwashed with diethyl ether
  5. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-91723533a6424cc5a8ee93cd5d4d312a
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07923450B2

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