4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole → HCID 59592998, compound

HRID 2098790Notes

Reaction equation

HRID 2098790 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[C:5]2[S:10][C:9]([CH2:11][O:12][CH2:13][C:14]([N:16]([CH3:18])[CH3:17])=[O:15])=[CH:8][C:6]=2[N:7]=1.CC1(C)C(C)(C)OB([C:33]2[CH:41]=[CH:40][CH:39]=[C:38]3[C:34]=2[CH:35]=[N:36][NH:37]3)O1>>[NH:37]1[C:38]2[C:34](=[C:33]([C:2]3[N:3]=[C:4]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)[C:5]4[S:10][C:9]([CH2:11][O:12][CH2:13][C:14]([N:16]([CH3:18])[CH3:17])=[O:15])=[CH:8][C:6]=4[N:7]=3)[CH:41]=[CH:40][CH:39]=2)[CH:35]=[N:36]1

Participants

3

Reactant 2

HCID 454801864-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazoleHCID 86618432HCID 86618432, compound

Product 1

HCID 59592998HCID 59592998, compound

Procedure

2-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethoxy)-N,N-dimethyl-acetamide was reacted with 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indazole in general procedure A. Purification by column chromatography yielded 333. NMR: CDCl3: 3.02 (6 H, s, Me), 3.96-3.99 (4 H, m, CH2), 4.09-4.13 (4 H, m, CH2), 4.31 (2 H, s, CH2), 4.95 (2 H, s, CH2), 7.45 (1 H, s, Ar), 7.50 (1 H, apparent triplet, J 8.2, Ar), 7.61 (1 H, d, J 8.2, Ar), 8.28 (1 H, d, J 7.5, Ar), 9.03 (1 H, s, Ar) and 10.30 (1 H, s, NH). MS: (ESI+): MH+ 453.20

Workup

  1. customPurification by column chromatography

Sources & evidence

ORD record
ord-3ea27489844f42598fe2563f8cb468ff
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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