Trifluoroacetic acid → HCID 86345725, compound

HRID 1772678Notes

Reaction equation

HRID 1772678 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.[CH3:29][N:30]1[C:35](=[O:36])[N:34](COCC[Si](C)(C)C)[C:33]2[CH:45]=[CH:46][C:47](B3OC(C)(C)C(C)(C)O3)=[CH:48][C:32]=2[S:31]1(=[O:59])=[O:58].C(O)(C(F)(F)F)=O>>[CH3:29][N:30]1[C:35](=[O:36])[NH:34][C:33]2[CH:45]=[CH:46][C:47]([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:48][C:32]=2[S:31]1(=[O:59])=[O:58]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 117728505(E)-4-(5-Bromo-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-8-yl)morpholineHCID 131734683HCID 131734683, compound

Product 1

HCID 86345725HCID 86345725, compound

Procedure

Compound 2b was subjected to Suzuki coupling conditions using the methods described in Example 1, Step G, with compound 42c and the resulting product was deprotected with TFA using the methods described Example 37, Steps B and C to obtain the title compound 19. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 11.71 (s, 1H), 8.35 (d, J=8.6 Hz, 1H), 8.19 (s, 1H), 8.12 (s, 1H), 8.05 (d, J=8.6 Hz, 1H), 7.96 (t, J=8.6 Hz, 2H), 7.83-7.90 (m, 2H), 7.75 (t, J=7.6 Hz, 1H), 7.64 (d, J=16.2 Hz, 1H), 7.53-7.60 (m, 1H), 7.43-7.51 (m, 2H), 4.31 (br. s., 4H), 3.82 (br. s., 4H), 3.25 (s, 3H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C29H25N7O4S: 568.2 (M+H). Found 568.5.

Sources & evidence

ORD record
ord-48d153c8cb8844eeb88e152c26533240
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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