Trifluoroacetic acid → HCID 57965009, compound

HRID 1931619Notes

Reaction equation

HRID 1931619 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3=[N:19][CH:20]=[N:21][C:22]([NH:23][C:24]4[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][C:25]=4[F:34])=[C:17]3[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.[CH2:42](Br)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>ClCCl>[CH2:42]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]2[C:18]3=[N:19][CH:20]=[N:21][C:22]([NH:23][C:24]4[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:31])=[O:32])=[CH:26][C:25]=4[F:34])=[C:17]3[CH:16]=[N:15]2)[CH2:12][CH2:13]1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7498Benzyl BromideHCID 57544434HCID 57544434, compound

Product 1

HCID 57965009HCID 57965009, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[1-(1-Benzyl-piperidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]-(2-fluoro-4-methanesulfonylphenyl)-amine was prepared according to General Procedure F by the reaction of 4-[4-(2-fluoro-4-methanesulfonyl-phenylamino)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (Example 1) 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 1.87-1.90 (m, 2H), 2.13-2.24 (m, 4H), 2.93-2.97 (m, 2H), 3.54 (s, 2H), 4.67-4.72 (m, 1H), 7.25-7.35 (m, 5H), 7.78-7.81 (m, 1H), 7.88-7.91 (m, 1H), 8.20-8.24 (m, 1H), 8.38-8.41 (m, 2H), 11.71 (s, 1H). Mass spectrum MH+=481.

Sources & evidence

ORD record
ord-1539e4f678204222b6abf5f5fec5c09f
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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