5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridine → 4-(2-(3-(methylsulfonyl)phenyl)-5-(1H-pyrrolo[2,3-b]pyridin-5-yl)thiazolo[5,4-d]pyrimidin-7-yl)morpholine

HRID 1692769Notes

Reaction equation

HRID 1692769 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[C:5]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:12]=3)[S:8][C:6]=2[N:7]=1.CC1(C)C(C)(C)OB([C:35]2[CH:36]=[C:37]3[CH:43]=[CH:42][NH:41][C:38]3=[N:39][CH:40]=2)O1>>[CH3:20][S:17]([C:13]1[CH:12]=[C:11]([C:9]2[S:8][C:6]3[N:7]=[C:2]([C:35]4[CH:36]=[C:37]5[CH:43]=[CH:42][NH:41][C:38]5=[N:39][CH:40]=4)[N:3]=[C:4]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[C:5]=3[N:10]=2)[CH:16]=[CH:15][CH:14]=1)(=[O:19])=[O:18]

Participants

3

Reactant 2

HCID 242087895-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridineHCID 866300685-Chloro-2-(3-(methylsulfonyl)phenyl)-7-morpholinothiazolo[5,4-d]pyrimidine

Product 1

HCID 252541494-(2-(3-(methylsulfonyl)phenyl)-5-(1H-pyrrolo[2,3-b]pyridin-5-yl)thiazolo[5,4-d]pyrimidin-7-yl)morpholineYield 43.6%

Procedure

5-Chloro-2-(3-methanesulfonyl-phenyl)-7-morpholin-4-yl-thiazolo[5,4-d]pyrimidine (80 mg) was reacted with 54 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 41.8 mg of 109. MS (Q1) 493.2 (M)+.

Workup

  1. customThe product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-39ce2f4b901e47eab3a335b625832ad6
Source dataset
uspto-grants-2012_04
Patent number
US08158626B2

Reaction notes

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