Trifluoroacetic acid → (E)-1-Methyl-6-(8-morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-5-yl)-1,3-dihydrobenzo[c][1,2,5]thiadiazole 2,2-dioxide trifluoroacetic acid salt
Reaction equation
Br[C:2]1[N:7]2[CH:8]=[C:9](/[CH:11]=[CH: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[N:30]1[S:34](=[O:36])(=[O:35])[N:33]([CH2:37]OCC[Si](C)(C)C)[C:32]2[CH:45]=[CH:46][C:47](B3OC(C)(C)C(C)(C)O3)=[CH:48][C:31]1=2.[C:58]([OH:64])([C:60]([F:63])([F:62])[F:61])=[O:59]>>[F:61][C:60]([F:63])([F:62])[C:58]([OH:64])=[O:59].[CH3:37][N:33]1[C:32]2[CH:45]=[C:46]([C:2]3[N:7]4[CH:8]=[C:9](/[CH:11]=[CH:12]/[C:13]5[CH:22]=[CH:21][C:20]6[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=6)[N:14]=5)[N:10]=[C:6]4[C:5]([N:23]4[CH2:24][CH2:25][O:26][CH2:27][CH2:28]4)=[N:4][CH:3]=3)[CH:47]=[CH:48][C:31]=2[NH:30][S:34]1(=[O:35])=[O:36]Participants
4
Reactant 3
Product 1
Procedure
Compound 2b was subjected to Suzuki coupling conditions with (3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1,3-dihydrobenzo[c][1,2,5]thiadiazole 2,2-dioxide and the resulting product was deprotected with TFA using the methods described in Example 37, Steps B and C) to obtain the title compound 43. 1H NMR (400 MHz, CD3OD) δ (ppm): 8.79 (d, J=9.0 Hz, 1H), 8.28 (d, J=9.0 Hz, 1H), 8.07-8.18 (m, 4H), 8.02 (td, J=7.8, 1.2 Hz, 1H), 7.78-7.87 (m, 2H), 7.72 (s, 1H), 7.32 (s, 1H), 7.27 (dd, J=8.1, 2.0 Hz, 1H), 7.10 (d, J=1.7 Hz, 1H), 7.02 (d, J=8.1 Hz, 1H), 4.33-4.39 (m, 4H), 3.91-3.99 (m, 4H), 3.34 (s, 3H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C28H25N7O3S: 540.2 (M+H). Found 540.4.
Sources & evidence
- ORD record
- ord-1e9923979f3c4b9f8fa4817c79968b63
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09249163B2
Reaction notes
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