Triethylamine → 4-(2-Fluorophenyl)-N-(2-methylbenzothiazol-5-yl)-1-piperazine carboxamide

HRID 491572

반응식

HRID 491572 반응식
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH3:10])=[N:7][C:6]=2[CH:11]=1.C(N(CC)CC)C.ClC(Cl)(O[C:23](=[O:29])OC(Cl)(Cl)Cl)Cl.[F:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[N:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1>C(Cl)Cl>[F:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[N:38]1[CH2:43][CH2:42][N:41]([C:23]([NH:1][C:2]2[CH:3]=[CH:4][C:5]3[S:9][C:8]([CH3:10])=[N:7][C:6]=3[CH:11]=2)=[O:29])[CH2:40][CH2:39]1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 362295-Benzothiazolamine, 2-methyl-HCID 705291-(2-Fluorophenyl)piperazineHCID 94429Triphosgene

생성물 1

HCID 100905614-(2-Fluorophenyl)-N-(2-methylbenzothiazol-5-yl)-1-piperazine carboxamide수율 93.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 5-amino-2-methylbenzothiazole (100 mg, 0.61 mmol) and triethylamine (170 ul, 1.22 mmol) in DCM (5 ml) at 0° C. under an argon atmosphere was added triphosgene (60 mg, 0.2 mmol). The mixture was warmed to room temp. and stirred for 1 h. 4-(2-Fluorophenyl)piperazine (110 mg, 0.61 mmol) was added and the reaction was stirred at room temp. overnight. The solvent was removed in vacuo and the residue purified by chromatography eluting with a 0-100% EtOAc/petroleum ether gradient to give the title compound as a pale yellow solid (69 mg). 1H NMR (400 MHz, CDCl3) δ (ppm): 7.82 (d, 1H), 7.71 (d, 1H), 7.53 (dd, 1H), 6.92-7.10 (m, 4H), 6.65 (s, 1H), 3.69 (m, 2H), 3.13 (m, 2H), 2.81 (s, 3H). MS(ES): MH+ 371, M−H+ 369.

후처리

  1. temperatureThe mixture was warmed to room temp.
  2. stirringthe reaction was stirred at room temp. overnight
  3. customThe solvent was removed in vacuo
  4. customthe residue purified by chromatography
  5. washeluting with a 0-100% EtOAc/petroleum ether gradient

출처 및 근거

ORD 기록
ord-157e463f7efb4d5b9ea527d9ddd05e0f
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531558B2

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