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

HRID 1772662Notes

Reaction equation

HRID 1772662 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

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 90391711N-(tert-Butyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-sulfonamideHCID 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.

Sources & evidence

ORD record
ord-9584198b7a3a473da67ab990a9796e91
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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