[F:1][C:2]1[CH:16]=[CH:15][C:5]2[CH2:6][CH2:7][CH2:8][C:9]3[S:13][C:12]([NH2:14])=[N:11][C:10]=3[C:4]=2[CH:3]=1.C(N(CC)CC)C.[Br:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29](Cl)=[O:30]>C1COCC1.CN(C1C=CN=CC=1)C>[F:1][C:2]1[CH:16]=[CH:15][C:5]2[CH2:6][CH2:7][CH2:8][C:9]3[S:13][C:12]([NH:14][C:29](=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25][Br:24])=[N:11][C:10]=3[C:4]=2[CH:3]=19-Fluoro-5,6-dihydro-4H-benzo[6,7]cyclohepta[d][1,3]thiazol-2-amine (150 mg, 0.640 mmole) was dissolved in 3 ml of dry THF, mixed with triethylamine (135 μl, 0.970 mmole), cooled in an ice bath and treated with 5-bromovaleryl chloride (90 μl, 0.67 mmole). The mixture was stirred at room temperature for 3 days. TLC analysis of the mixture showed 50% completion. Hence, a catalytic amount of DMAP was added and stirring was continued for 16 hours. There was no change in the TLC of the mixture. 5-Bromovaleryl chloride (90 μl) was added and stirred for 3 days. The reaction mixture was partitioned between ethyl acetate and saturated sodium carbonate and the aqueous phase separated and extracted with 2×3 ml ethyl acetate. The combined ethyl acetate extracts were washed with saturated sodium chloride solution, concentrated and chromatographed (silica, Ethyl acetate/hexanes) to give 179 mg of the desired product as a white foam (70%): 397, 399 (ESMS, MH+).
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