Cl.[Cl:2][C:3]1[CH:4]=[C:5]([C:9]2([NH2:13])[CH2:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[N:32]([CH:33]3[CH2:35][CH2:34]3)[C:31](=[O:36])[N:30]([CH2:37][C:38](O)=[O:39])[N:29]=2)=[CH:24][CH:23]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C)C=O>[Cl:2][C:3]1[CH:4]=[C:5]([C:9]2([NH:13][C:38](=[O:39])[CH2:37][N:30]3[C:31](=[O:36])[N:32]([CH:33]4[CH2:34][CH2:35]4)[C:28]([C:25]4[CH:26]=[CH:27][C:22]([Cl:21])=[CH:23][CH:24]=4)=[N:29]3)[CH2:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=157.2 mg (0.262 mmol) of 1-(3-chlorophenyl)cyclobutanamine hydrochloride are placed in 2 ml of dimethylformamide and treated with 26.5 mg (0.262 mmol) of triethylamine. After 10 mins' stirring, 70.0 mg (0.238 mmol) of [3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetic acid from Example 88A and 38.7 mg (0.286 mmol) of HOBt are added. After a further 10 mins' stirring, the mixture is treated with 59.4 mg (0.310 mmol) of EDC hydrochloride and stirred overnight at room temperature. For the workup, the reaction mixture is partitioned between dichloromethane and water, and the organic phase is separated, dried over sodium sulphate and concentrated. The residue is purified by flash chromatography on silica gel (eluent: dichloromethane/methanol first 200:1, then 100:1) and thus yields 66 mg (61% of theory) of the target compound.
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