1-(4-(4-Hydroxyphenyl)piperazin-1-yl)ethanone → 4-{4-[4-(4-Acetyl-piperazin-1-yl)-phenoxy]-pyrazolo[3,4-d]pyrimidin-1-yl}-piperidine-1-carboxylic acid tert-butyl ester

HRID 1931674Notes

Reaction equation

HRID 1931674 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3=[N:19][CH:20]=[N:21][C:22](Cl)=[C:17]3[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:24]([N:27]1[CH2:32][CH2:31][N:30]([C:33]2[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=2)[CH2:29][CH2:28]1)(=[O:26])[CH3:25]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3=[N:19][CH:20]=[N:21][C:22]([O:39][C:36]4[CH:35]=[CH:34][C:33]([N:30]5[CH2:29][CH2:28][N:27]([C:24](=[O:26])[CH3:25])[CH2:32][CH2:31]5)=[CH:38][CH:37]=4)=[C:17]3[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 7124411-(4-(4-Hydroxyphenyl)piperazin-1-yl)ethanoneHCID 57964905Tert-butyl 4-(4-chloro-1H-pyrazolo[3,4-D]pyrimidin-1-YL)piperidine-1-carboxylate2×

Product 1

HCID 532583604-{4-[4-(4-Acetyl-piperazin-1-yl)-phenoxy]-pyrazolo[3,4-d]pyrimidin-1-yl}-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-{4-[4-(4-Acetyl-piperazin-1-yl)-phenoxy]-pyrazolo[3,4-d]pyrimidin-1-yl}-piperidine-1-carboxylic acid tert-butyl ester was prepared according to General Procedure B by the reaction of 4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 19) with 1-acetyl-4-(4-hydroxyphenyl)piperazine (available from Aldrich Chemical Company, Inc., Milwaukee, Wis., USA) in dimethylformamide. 1H NMR (400 MHz, DMSO-d6) δ 1.43 (s, 9H), 1.94-2.01 (m, 4H), 2.05 (s, 3H), 2.93-3.02 (m, 2H), 3.10-3.20 (m, 4H), 3.55-3.65 (m, 4H), 4.08-4.11 (m, 2H), 4.96-5.01 (m, 1H), 7.04-7.08 (m, 2H), 7.17-7.20 (m, 2H), 7.95 (s, 1H), 8.53 (s, 1H). Mass spectrum M+Na=544, MH+=522.

Sources & evidence

ORD record
ord-8ccb7e176b2049ad9278bcf44cb83ee6
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

Loading…