3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline → 4-(2-((4-(Methylsulfonyl)piperazin-1-yl)methyl)-5-(quinolin-3-yl)thiazolo[5,4-d]pyrimidin-7-yl)morpholine

HRID 1692771Notes

Reaction equation

HRID 1692771 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[C:5]2[N:10]=[C:9]([CH2:11][N:12]3[CH2:17][CH2:16][N:15]([S:18]([CH3:21])(=[O:20])=[O:19])[CH2:14][CH2:13]3)[S:8][C:6]=2[N:7]=1.CC1(C)C(C)(C)OB([C:36]2[CH:37]=[N:38][C:39]3[C:44]([CH:45]=2)=[CH:43][CH:42]=[CH:41][CH:40]=3)O1>>[CH3:21][S:18]([N:15]1[CH2:16][CH2:17][N:12]([CH2:11][C:9]2[S:8][C:6]3[N:7]=[C:2]([C:36]4[CH:37]=[N:38][C:39]5[C:44]([CH:45]=4)=[CH:43][CH:42]=[CH:41][CH:40]=5)[N:3]=[C:4]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[C:5]=3[N:10]=2)[CH2:13][CH2:14]1)(=[O:20])=[O:19]

Participants

3

Reactant 2

HCID 108485903-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinolineHCID 445416755-Chloro-2-((4-methylsulfonylpiperazin-1-yl)methyl)-7-morpholinothiazolo[5,4-d]pyrimidine

Product 1

HCID 252541524-(2-((4-(Methylsulfonyl)piperazin-1-yl)methyl)-5-(quinolin-3-yl)thiazolo[5,4-d]pyrimidin-7-yl)morpholineYield 46%

Procedure

5-Chloro-2-(4-methanesulfonyl-piperazin-1-ylmethyl)-7-morpholin-4-yl-thiazolo[5,4-d]pyrimidine (130 mg) was reacted with 92 mg of 3-(4,4,5,5-tetramethyl-1,3,2,-dioxaborolan-2-yl)quinoline via General Procedure A. The product was purified by reverse phase HPLC to yield 72.6 mg of 112. MS (Q1) 526.2 (M)+.

Workup

  1. customThe product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-03a4c91261e04da086da6570ec19fd26
Source dataset
uspto-grants-2012_04
Patent number
US08158626B2

Reaction notes

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