5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridine → HCID 24969049, compound

HRID 2098874Notes

Reaction equation

HRID 2098874 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[C:5]2[S:10][C:9]([C:11]3[CH:12]=[C:13]([CH:20]=[CH:21][CH:22]=3)[C:14]([NH:16][CH2:17][CH2:18][OH:19])=[O:15])=[C:8]([CH3:23])[C:6]=2[N:7]=1.[NH:30]1[C:38]2[C:33](=[CH:34][C:35](B3OC(C)(C)C(C)(C)O3)=[CH:36][N:37]=2)[CH:32]=[CH:31]1>>[OH:19][CH2:18][CH2:17][NH:16][C:14](=[O:15])[C:13]1[CH:20]=[CH:21][CH:22]=[C:11]([C:9]2[S:10][C:5]3[C:4]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)=[N:3][C:2]([C:35]4[CH:34]=[C:33]5[CH:32]=[CH:31][NH:30][C:38]5=[N:37][CH:36]=4)=[N:7][C:6]=3[C:8]=2[CH3:23])[CH:12]=1

Participants

3

Reactant 2

HCID 242087895-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridineHCID 86618457HCID 86618457, compound

Product 1

HCID 24969049HCID 24969049, compound

Procedure

3-(2-Chloro-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-6-yl)benzoic acid (60 mg) was reacted with ethanolamine via General Procedure B to yield 3-(2-chloro-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-6-yl)-N-(2-hydroxyethyl)benzamide. Crude 3-(2-chloro-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-6-yl)-N-(2-hydroxyethyl)benzamide (74 mg) was coupled to 7-azaindole-5-boronic acid pinacol ester via General Procedure A. The product was purified by reverse phase HPLC to yield 2.6 mg of 426. MS (Q1) 515.2 (M)+

Workup

  1. customThe product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-fc77c08849c445fdb4f02e9e5353a00a
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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