(3-{[(Methanesulfonyl)amino]methyl}phenyl)boronic acid → n-Methylsulfonyl(3-(7-methyl-4-morpholino-2-(1h-pyrrolo[2,3-b]pyridin-5-yl)thieno[3,2-d]pyrimidin-6-yl)phenyl)methanamine

HRID 2262302Notes

Reaction equation

HRID 2262302 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[S:10][C:9](I)=[C:8]([CH3:12])[C:6]=2[N:7]=1.[CH3:19][S:20]([NH:23][CH2:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=1)(=[O:22])=[O:21].[NH:34]1[C:42]2[C:37](=[CH:38][C:39](B3OC(C)(C)C(C)(C)O3)=[CH:40][N:41]=2)[CH:36]=[CH:35]1>>[CH3:19][S:20]([NH:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[C:29]([C:9]2[S:10][C:5]3[C:4]([N:13]4[CH2:18][CH2:17][O:16][CH2:15][CH2:14]4)=[N:3][C:2]([C:39]4[CH:38]=[C:37]5[CH:36]=[CH:35][NH:34][C:42]5=[N:41][CH:40]=4)=[N:7][C:6]=3[C:8]=2[CH3:12])[CH:30]=1)(=[O:22])=[O:21]

Participants

4

Reactant 3

HCID 22309453(3-{[(Methanesulfonyl)amino]methyl}phenyl)boronic acidHCID 242087895-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridineHCID 595928802-Chloro-6-iodo-7-methyl-4-morpholinothieno[3,2-d]pyrimidine

Product 1

HCID 59592861n-Methylsulfonyl(3-(7-methyl-4-morpholino-2-(1h-pyrrolo[2,3-b]pyridin-5-yl)thieno[3,2-d]pyrimidin-6-yl)phenyl)methanamine

Procedure

2-Chloro-6-iodo-7-methyl-4-morpholinothieno[3,2-d]pyrimidine (50 mg) was coupled to 3-methanesulphonylamino methyl benzeneboronic acid, and then reacted with 7-azaindole-5-boronic acid pinacol ester via General Procedure F. The product was purified by reverse phase HPLC to yield 34.5 mg of 424. MS (Q1) 535.2 (M)+

Workup

  1. customThe product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-cf41e71b66264160990200fa715a20db
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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