4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole → HCID 59593057, compound

HRID 2098833Notes

Reaction equation

HRID 2098833 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][NH:12][CH2:13][CH2:14][S:15]([CH3:18])(=[O:17])=[O:16])=[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][NH:12][CH2:13][CH2:14][S:15]([CH3:18])(=[O:17])=[O:16])=[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 86618448HCID 86618448, compound

Product 1

HCID 59593057HCID 59593057, compound

Procedure

(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-(2-methanesulfonyl-ethyl)-amine 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 383. NMR: CDCl3: 2.95 (3 H, s, Me), 3.18-3.21 (4 H, m, CH2), 3.82-3.85 (4 H, m, CH2), 4.01-4.04 (4 H, m, CH2), 4.12 (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) and 9.03 (1 H, s, Ar). MS: (ESI+): MH+ 473.22

Workup

  1. customPurification by column chromatography

Sources & evidence

ORD record
ord-d9e09c05b802488f951ffe27f0601a92
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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