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

HRID 1772618Notes

Reaction equation

HRID 1772618 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[C:45](=[O:46])[N:44]([CH2:47][O:48][CH2:49][CH2:50][Si:51]([CH3:54])([CH3:53])[CH3:52])[NH:43][NH:42]3)=[CH:37][CH:36]=2)OC1(C)C>>[O:26]1[CH2:27][CH2:28][N:23]([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:40]=[CH:39][C:38]([N:41]4[C:45](=[O:46])[N:44]([CH2:47][O:48][CH2:49][CH2:50][Si:51]([CH3:54])([CH3:53])[CH3:52])[N:43]=[N:42]4)=[CH:37][CH:36]=3)=[CH:3][N:4]=2)[CH2:24][CH2:25]1

Participants

3

Reactant 2

HCID 1177278954-(5-Bromo-2-(2-(quinolin-2-yl)ethyl)imidazo[1,2-a]pyrazin-8-yl)morpholineHCID 1317346711-[4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4-[[2-(trimethylsilyl)ethoxy]methyl]-1,2,3,4-tetrazolidin-5-one

Product 1

HCID 1232142681-(4-(8-Morpholino-2-(2-(quinolin-2-yl)ethyl)imidazo[1,2-a]pyrazin-5-yl)phenyl)-4-((2-(trimethylsilyl)ethoxy)methyl)-1H-tetrazol-5(4H)-oneYield 31.6%

Procedure

Compound 3a (500 mg, 1.15 mmol) was subjected to Suzuki coupling conditions with 1-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4-[[2-(trimethylsilyl)ethoxy]methyl]-1,2,3,4-tetrazolidin-5-one (1.44 g, 3.45 mmol) using the reaction conditions described in Example 1, Step G to obtain compound 14d as a white solid (236 mg, 31% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C34H39N9O3Si: 650.3 (M+H). Found 650.4.

Workup

  1. customthe reaction conditions

Sources & evidence

ORD record
ord-d2d0ee1aa066423aafdf52f9e5c98532
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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