4-(5-Bromo-2-(2-(quinolin-2-yl)ethyl)imidazo[1,2-a]pyrazin-8-yl)morpholine → 1-[4-[8-(Morpholin-4-yl)-2-[2-(quinolin-2-yl)ethyl]imidazo[1,2-a]pyrazin-5-yl]phenyl]-2-[[2-(trimethylsilyl)ethoxy]methyl]-2,3-dihydro-1H-1,2,4-triazol-3-one

HRID 1772613Notes

Reaction equation

HRID 1772613 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)OB([C:35]2[CH:40]=[CH:39][C:38]([N:41]3[CH:45]=[N:44][C:43](=[O:46])[N:42]3[CH2:47][O:48][CH2:49][CH2:50][Si:51]([CH3:54])([CH3:53])[CH3:52])=[CH:37][CH:36]=2)OC1(C)C>>[N:23]1([C:5]2[C:6]3[N:7]([CH:8]=[C:9]([CH2:11][CH2:12][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:35]3[CH:36]=[CH:37][C:38]([N:41]4[CH:45]=[N:44][C:43](=[O:46])[N:42]4[CH2:47][O:48][CH2:49][CH2:50][Si:51]([CH3:54])([CH3:53])[CH3:52])=[CH:39][CH:40]=3)=[CH:3][N:4]=2)[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1

Participants

3

Reactant 2

HCID 1177278954-(5-Bromo-2-(2-(quinolin-2-yl)ethyl)imidazo[1,2-a]pyrazin-8-yl)morpholineHCID 1235782711-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-2-[[2-(trimethylsilyl)ethoxy]methyl]-2,3-dihydro-1H-1,2,4-triazol-3-one

Product 1

HCID 1233261671-[4-[8-(Morpholin-4-yl)-2-[2-(quinolin-2-yl)ethyl]imidazo[1,2-a]pyrazin-5-yl]phenyl]-2-[[2-(trimethylsilyl)ethoxy]methyl]-2,3-dihydro-1H-1,2,4-triazol-3-oneYield 25.1%

Procedure

Compound 3a (400 mg, 0.910 mmol) was subjected to Suzuki coupling conditions with 1-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-2-[[2-(trimethylsilyl)ethoxy]methyl]-2,3-dihydro-1H-1,2,4-triazol-3-one (1.14 g, 2.73 mmol) using the reaction conditions described in Example 1, Step G to obtain compound 11e as a brown solid (148 mg, 25% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C35H40N8O3Si: 649.3 (M+H). Found 649.3.

Workup

  1. customthe reaction conditions

Sources & evidence

ORD record
ord-c5b0cc64d1594359881792f8ceeaeb42
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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