(E)-4-(5-Bromo-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-8-yl)morpholine → HCID 86345726, compound

HRID 1772675Notes

Reaction equation

HRID 1772675 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]([CH3:37])[C:33]2[CH:38]=[CH:39][C:40](B3OC(C)(C)C(C)(C)O3)=[CH:41][C:32]=2[S:31]1(=[O:52])=[O:51]>>[CH3:29][N:30]1[C:35](=[O:36])[N:34]([CH3:37])[C:33]2[CH:38]=[CH:39][C:40]([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:41][C:32]=2[S:31]1(=[O:51])=[O:52]

Participants

3

Reactant 2

HCID 117728505(E)-4-(5-Bromo-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-8-yl)morpholineHCID 131734681HCID 131734681, compound

Product 1

HCID 86345726HCID 86345726, compound

Procedure

Compound 2b was subjected to Suzuki coupling conditions using the methods described in Example 1, Step G, with compound 41b to obtain the title compound 20. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.35 (d, J=8.6 Hz, 1H), 8.18-8.20 (m, 2H), 8.15 (dd, J=8.6, 2.0 Hz, 1H), 7.96 (t, J=8.6 Hz, 2H), 7.90 (s, 1H), 7.86 (d, J=6.6 Hz, 1H), 7.72-7.80 (m, 2H), 7.64 (d, J=16.2 Hz, 1H), 7.56 (t, J=7.3 Hz, 1H), 7.49 (s, 1H), 4.31 (m, 4H), 3.80-3.86 (m, 4H), 3.58 (s, 3H), 3.28 (s, 3H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C30H27N7O4S: 582.2 (M+H). Found 582.4.

Sources & evidence

ORD record
ord-d3e71f0ff961457babff6a64d275f7a1
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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