Pyridine → 4-(4-chlorophenyl)-N-(2-methylbenzothiazol-5-yl)cyclohexane-1-carboxamide

HRID 491571

Reaction equation

[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

Participants

Conditions

Temperature: 45 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-33710b17ac3a426daf7d3f18064a41b1
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07531558B2

Linked notes

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