Trifluoroacetic acid → 5-(8-Morpholino-2-((quinolin-2-yloxy)methyl)imidazo[1,2-a]pyrazin-5-yl)pyridine-2-sulfonamide trifluoroacetic acid salt

Reaction equation

Br[C:2]1[N:7]2[CH:8]=[C:9]([CH2:11][O:12][C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]=3)[N:10]=[C:6]2[C:5]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[N:4][CH:3]=1.C([NH:33][S:34]([C:37]1[CH:42]=[CH:41][C:40](B2OC(C)(C)C(C)(C)O2)=[CH:39][N:38]=1)(=[O:36])=[O:35])(C)(C)C.[C:52]([OH:58])([C:54]([F:57])([F:56])[F:55])=[O:53]>>[F:55][C:54]([F:57])([F:56])[C:52]([OH:58])=[O:53].[O:26]1[CH2:27][CH2:28][N:23]([C:5]2[C:6]3[N:7]([CH:8]=[C:9]([CH2:11][O:12][C:13]4[CH:22]=[CH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[N:14]=4)[N:10]=3)[C:2]([C:40]3[CH:41]=[CH:42][C:37]([S:34]([NH2:33])(=[O:36])=[O:35])=[N:38][CH:39]=3)=[CH:3][N:4]=2)[CH2:24][CH2:25]1

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 90391711N-(tert-Butyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-sulfonamide

HCID 117728336HCID 117728336, compound

Product 1

HCID 863456435-(8-Morpholino-2-((quinolin-2-yloxy)methyl)imidazo[1,2-a]pyrazin-5-yl)pyridine-2-sulfonamide trifluoroacetic acid salt

Procedure

Compound 31b was subjected to Suzuki coupling reaction conditions with compound 32b using the methods described in Example 1, Step G, and the resulting product was subjected to TFA deprotection using the methods described in Example 1, Step E, to obtain title compound 86. 1H-NMR (400 MHz, CD3OD) δ (ppm): 8.85 (s, 1H), 8.08-8.15 (m, 2H), 8.03 (d, J=9.0 Hz, 1H), 7.84 (s, 1H), 7.79 (d, J=8.6 Hz, 1H), 7.72 (d, J=7.4 Hz, 1H), 7.59-7.65 (m, 1H), 7.43 (s, 1H), 7.35-7.41 (m, 2H), 6.95 (d, J=9.0 Hz, 1H), 5.64 (s, 2H), 4.32 (br. s., 4H), 3.88 (m, 4H). Mass Spectrum (LCMS, ESI pos.) Calcd. for C25H23N7O4S: 518.1 (M+H). Found 518.2.