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

HRID 491572

反応式

HRID 491572 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-157e463f7efb4d5b9ea527d9ddd05e0f
出典データセット
uspto-grants-2009_05
特許番号
US07531558B2

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