5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridine → N-(3-(7-morpholino-5-(1H-pyrrolo[2,3-b]pyridin-5-yl)thiazolo[5,4-d]pyrimidin-2-yl)benzyl)methanesulfonamide

HRID 1692773Notes

Reaction equation

HRID 1692773 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[C:5]2[N:10]=[C:9]([C:11]3[CH:12]=[C:13]([CH:20]=[CH:21][CH:22]=3)[CH2:14][NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[S:8][C:6]=2[N:7]=1.CC1(C)C(C)(C)OB([C:37]2[CH:38]=[C:39]3[CH:45]=[CH:44][NH:43][C:40]3=[N:41][CH:42]=2)O1>>[O:26]1[CH2:27][CH2:28][N:23]([C:4]2[C:5]3[N:10]=[C:9]([C:11]4[CH:12]=[C:13]([CH:20]=[CH:21][CH:22]=4)[CH2:14][NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[S:8][C:6]=3[N:7]=[C:2]([C:37]3[CH:38]=[C:39]4[CH:45]=[CH:44][NH:43][C:40]4=[N:41][CH:42]=3)[N:3]=2)[CH2:24][CH2:25]1

Participants

3

Reactant 2

HCID 242087895-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridineHCID 86630071HCID 86630071, compound

Product 1

HCID 25254300N-(3-(7-morpholino-5-(1H-pyrrolo[2,3-b]pyridin-5-yl)thiazolo[5,4-d]pyrimidin-2-yl)benzyl)methanesulfonamideYield 31.6%

Procedure

N-[3-(5-Chloro-7-morpholin-4-yl-thiazolo[5,4-d]pyrimidin-2-yl)-benzyl]-methanesulfonamide (120 mg) was reacted with 80 mg of 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine via General Procedure A. The product was purified by reverse phase HPLC to yield 45 mg of 115. MS (Q1) 522.2 (M)+.

Workup

  1. customThe product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-fd0b2123b3db4d36a1bde10fc80bef1d
Source dataset
uspto-grants-2012_04
Patent number
US08158626B2

Reaction notes

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