反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.N1C=CC=CC=1.[NH2:29][C:30]1[CH:31]=[CH:32][C:33]2[S:37][C:36]([CH3:38])=[N:35][C:34]=2[CH:39]=1>C(Cl)Cl.CO.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:9][CH2:10][CH:11]([C:14]([NH:29][C:30]3[CH:31]=[CH:32][C:33]4[S:37][C:36]([CH3:38])=[N:35][C:34]=4[CH:39]=3)=[O:16])[CH2:12][CH2:13]2)=[CH:6][CH:7]=1参加物
反応物 4
生成物 1
試薬・触媒・溶媒 3
反応条件
- 温度
- 45 °C
実験手順
A suspension of 4-(4-chlorophenyl)-cyclohexane-1-carboxylic acid (100 mg, 0.42 mmol) in DCM (10 ml) was treated with catalytic DMF and oxalyl chloride (110 ul, 1.26 mmol) at 0° C. and the mixture was then stirred at room temp. for 1 h and at 45° C. for 2 h. The solvent and excess oxalyl chloride was removed in vacuo and the residue resuspended in DCM (5 ml). To this was added pyridine (35 ul, 0.42 mmol) and 5-amino-2-methylbenzothiazole (63 mg, 0.38 mmol) and the reaction stirred at room temp. overnight. MeOH (1 ml) was added and the mixture was washed with sat. aq. sodium bicarbonate solution and brine then dried (MgSO4) and concentrated to give the title compound as an off-white solid (148 mg). 1H NMR (400 MHz, DMSO) δ (ppm): 8.37 (d, 1H), 7.96 (d, 1H), 7.63 (dd, 1H), 7.40 (d, 2H), 7.38 (d, 2H), 2.83 (s, 3H), 2.49-2.63 (m, 2H), 2.04 (m, 2H), 1.94 (m, 2H), 1.69 (m, 2H), 1.53 (m, 2H). MS(ES): MH+ 385/387, M−H+ 383/385.
後処理
- customThe solvent and excess oxalyl chloride was removed in vacuo
- stirringthe reaction stirred at room temp. overnight
- washthe mixture was washed with sat. aq. sodium bicarbonate solution and brine
- dry with materialthen dried (MgSO4)
- concentrationconcentrated
出典と根拠
- ORDレコード
- ord-33710b17ac3a426daf7d3f18064a41b1
- 出典データセット
- uspto-grants-2009_05
- 特許番号
- US07531558B2
関連ノート
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