C(OC(=O)[NH:7][C@H:8]1[CH2:39][CH2:38][C:11]2[N:12]=[C:13]([NH:15][C:16](=[O:37])[C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][N:24]4[CH:28]=[C:27]([C:29]5[CH:34]=[CH:33][C:32]([C:35]#[N:36])=[CH:31][CH:30]=5)[CH:26]=[N:25]4)[CH:18]=3)[S:14][C:10]=2[CH2:9]1)(C)(C)C.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH2:7][C@H:8]1[CH2:39][CH2:38][C:11]2[N:12]=[C:13]([NH:15][C:16](=[O:37])[C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][N:24]4[CH:28]=[C:27]([C:29]5[CH:30]=[CH:31][C:32]([C:35]#[N:36])=[CH:33][CH:34]=5)[CH:26]=[N:25]4)[CH:18]=3)[S:14][C:10]=2[CH2:9]1Stir ((S)-2-{3-[4-(4-cyano-phenyl)-pyrazol-1-ylmethyl]-benzoylamino}-4,5,6,7-tetrahydro-benzothiazol-6-yl)-carbamic acid tert-butyl ester (0.38 g, 0.69 mmol) in 2 mL CH2Cl2 and 2 mL TFA for 3 h in a capped flask. Concentrate the reaction and bring to alkaline pH with aq. Na2CO3. Triturate the residue with CH2Cl2 and filter the product to give 0.23 g 75% yield of N—((S)-6-amino-4,5,6,7-tetrahydro-benzothiazol-2-yl)-3-[4-(4-cyano-phenyl)-pyrazol-1-ylmethyl]-benzamide as a beige solid. MS, ES+ 455.73 (M+H), rt 1.39 min.
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