Trifluoroacetic acid → 1-(1-Benzyl-piperidin-4-yl)-4-(4-methanesulfonyl-phenoxy)-1H-pyrazolo[3,4-d]pyrimidine

HRID 1931760Notes

Reaction equation

HRID 1931760 reaction equation
C(O[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:23][C:24]4[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=4)=[C:17]3[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(Br)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>ClCCl>[CH2:6]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]2[C:18]3=[N:19][CH:20]=[N:21][C:22]([O:23][C:24]4[CH:25]=[CH:26][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:28][CH:29]=4)=[C:17]3[CH:16]=[N:15]2)[CH2:12][CH2:13]1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7498Benzyl BromideHCID 532576834-[4-(4-Methanesulfonyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 579650401-(1-Benzyl-piperidin-4-yl)-4-(4-methanesulfonyl-phenoxy)-1H-pyrazolo[3,4-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(1-Benzyl-piperidin-4-yl)-4-(4-methanesulfonyl-phenoxy)-1H-pyrazolo[3,4-d]pyrimidine was prepared according to General Procedure F by the reaction of 4-[4-(4-methanesulfonyl-phenoxy)pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (Example 59) with trifluoroacetic acid in dichloromethane followed by reaction with benzyl bromide (available from Aldrich Chemical Company, Inc., Milwaukee, Wis., USA). 1H NMR (400 MHz, DMSO-d6) δ 1.93-1.99 (m, 2H), 2.20-2.22 (m, 4H), 2.93-2.99 (m, 2H), 3.30 (methyl sulfonyl and water peak), 3.55 (s, 2H), 4.75-4.81 (m, 1H), 7.26-7.35 (m, 5H), 7.62-7.64 (m, 2H), 8.04-8.06 (m, 2H), 8.37 (s, 1H), 8.55 (s, 1H). Mass spectrum MH+=464.

Sources & evidence

ORD record
ord-c5b4dfe85fd64a1cab52e9eabb5f7bda
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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