반응식
[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]=1참가 물질
반응물 4
생성물 1
시약·촉매·용매 3
반응 조건
- 온도
- 45 °C
실험 절차
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.
후처리
- 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
출처 및 근거
- ORD 기록
- ord-33710b17ac3a426daf7d3f18064a41b1
- 출처 데이터셋
- uspto-grants-2009_05
- 특허 번호
- US07531558B2
연결된 노트
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