5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridine → HCID 59592876, compound

HRID 2098869Notes

Reaction equation

HRID 2098869 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[C:5]2[S:10][C:9]([C:11]3[CH:12]=[C:13]([CH2:17][NH:18][C:19](=[O:23])[C@@H:20]([OH:22])[CH3:21])[CH:14]=[CH:15][CH:16]=3)=[C:8]([CH3:24])[C:6]=2[N:7]=1.[NH:31]1[C:39]2[C:34](=[CH:35][C:36](B3OC(C)(C)C(C)(C)O3)=[CH:37][N:38]=2)[CH:33]=[CH:32]1>>[OH:22][C@@H:20]([CH3:21])[C:19]([NH:18][CH2:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:9]2[S:10][C:5]3[C:4]([N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)=[N:3][C:2]([C:36]4[CH:35]=[C:34]5[CH:33]=[CH:32][NH:31][C:39]5=[N:38][CH:37]=4)=[N:7][C:6]=3[C:8]=2[CH3:24])[CH:12]=1)=[O:23]

Participants

3

Reactant 2

HCID 242087895-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridineHCID 87302845HCID 87302845, compound

Product 1

HCID 59592876HCID 59592876, compound

Procedure

Crude (2S)-N-(3-(2-chloro-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-6-yl)phenyl)methyl-2-hydroxypropanamide (65 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 48.4 mg of 421. MS (Q1) 529.2 (M)+

Workup

  1. customThe product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-955b864576c64a18899f27fdfdb65482
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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