5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridine → HCID 24969048, compound

HRID 2262304Notes

Reaction equation

HRID 2262304 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[C:5]2[S:10][C:9]([C:11]3[CH:12]=[C:13]([C:17]([N:19]4[CH2:24][CH2:23][CH:22]([OH:25])[CH2:21][CH2:20]4)=[O:18])[CH:14]=[CH:15][CH:16]=3)=[C:8]([CH3:26])[C:6]=2[N:7]=1.[NH:33]1[C:41]2[C:36](=[CH:37][C:38](B3OC(C)(C)C(C)(C)O3)=[CH:39][N:40]=2)[CH:35]=[CH:34]1>>[OH:25][CH:22]1[CH2:23][CH2:24][N:19]([C:17]([C:13]2[CH:14]=[CH:15][CH:16]=[C:11]([C:9]3[S:10][C:5]4[C:4]([N:27]5[CH2:32][CH2:31][O:30][CH2:29][CH2:28]5)=[N:3][C:2]([C:38]5[CH:37]=[C:36]6[CH:35]=[CH:34][NH:33][C:41]6=[N:40][CH:39]=5)=[N:7][C:6]=4[C:8]=3[CH3:26])[CH:12]=2)=[O:18])[CH2:20][CH2:21]1

Participants

3

Reactant 2

HCID 242087895-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridineHCID 86618455HCID 86618455, compound

Product 1

HCID 24969048HCID 24969048, compound

Procedure

3-(2-Chloro-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-6-yl)benzoic acid (60 mg) was reacted with 4-hydroxypiperidine via General Procedure B to yield 3-(2-chloro-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-6-yl)phenyl(4-hydroxypiperidin-1-yl)methanone. Crude 3-(2-chloro-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-6-yl)phenyl(4-hydroxypiperidin-1-yl)methanone (72 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 29.5 mg of 425. MS (Q1) 555.2 (M)+

Workup

  1. customThe product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-22eeee9d20d347cbb60b1eae29ad8ed8
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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