4-(5-Bromo-2-(2-(quinolin-2-yl)ethyl)imidazo[1,2-a]pyrazin-8-yl)morpholine → HCID 178419989, compound

HRID 1772709Notes

Reaction equation

HRID 1772709 reaction equation
Br[C:2]1[N:7]2[CH:8]=[C:9]([CH2:11][CH2:12][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.CC1(C)C(C)(C)OB([C:37]2[CH:42]=[CH:41][C:40]([S:43][C:44]3[N:48](COCC[Si](C)(C)C)[N:47]=[N:46][CH:45]=3)=[CH:39][CH:38]=2)O1>>[NH:48]1[C:44]([S:43][C:40]2[CH:41]=[CH:42][C:37]([C:2]3[N:7]4[CH:8]=[C:9]([CH2:11][CH2:12][C:13]5[CH:22]=[CH:21][C:20]6[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=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:38][CH:39]=2)=[CH:45][N:46]=[N:47]1

Participants

3

Reactant 2

HCID 1177278954-(5-Bromo-2-(2-(quinolin-2-yl)ethyl)imidazo[1,2-a]pyrazin-8-yl)morpholineHCID 123519997HCID 123519997, compound

Product 1

HCID 178419989HCID 178419989, compound

Procedure

The title compound 36 was prepared from compound 3a and compound 63c using the methods described in Example 1, Step G. Subsequently, the SEM group was removed using the methods described in Example 37, Step C. 1H-NMR (400 MHz CDCl3) δ (ppm): 3.22-3.32 (m, 2H), 3.35-3.43 (m, 2H), 3.83 (br. s., 4H), 4.14 (br. s., 4H), 7.17-7.30 (m, 3H), 7.31-7.39 (m, 4H), 7.48-7.59 (m, 1H), 7.73 (br. s., 1H), 7.76-7.88 (m, 2H), 8.01 (d, J=8.6 Hz, 1H), 8.10 (d, J=8.6 Hz, 1H). Mass Spectrum LCMS, ESI (pos.) Calcd. for C29H26N8OS: 535.0 [M+H]. found 535.6.

Workup

  1. customSubsequently, the SEM group was removed

Sources & evidence

ORD record
ord-cb3e96441c8c49dbb3818ffa210edda0
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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