4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole → N-(2-(1H-indazol-4-yl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)-2-methoxyacetamide

HRID 2098626Notes

Reaction equation

HRID 2098626 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[C:5]2[S:10][C:9]([NH:11][C:12](=[O:16])[CH2:13][O:14][CH3:15])=[CH:8][C:6]=2[N:7]=1.CC1(C)C(C)(C)OB([C:31]2[CH:39]=[CH:38][CH:37]=[C:36]3[C:32]=2[CH:33]=[N:34][NH:35]3)O1>>[NH:35]1[C:36]2[C:32](=[C:31]([C:2]3[N:3]=[C:4]([N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)[C:5]4[S:10][C:9]([NH:11][C:12](=[O:16])[CH2:13][O:14][CH3:15])=[CH:8][C:6]=4[N:7]=3)[CH:39]=[CH:38][CH:37]=2)[CH:33]=[N:34]1

Participants

3

Reactant 2

HCID 454801864-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazoleHCID 86618373N-(2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)-2-methoxyacetamide

Product 1

HCID 59592951N-(2-(1H-indazol-4-yl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)-2-methoxyacetamide

Procedure

70 mg of crude N-(2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)-2-methoxyacetamide was coupled to 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole 7 via General Procedure A. The product was purified by reverse phase HPLC to yield 28.1 mg of 119. MS (Q1) 425 (M)+

Workup

  1. customThe product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-236960aa8cc84e5db68640ab06f7aefe
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

Loading…