Trifluoroacetic acid → 2,2,2-Trifluoro-1-{4-[4-(4-methanesulfonyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidin-1-yl}-ethanone

HRID 1931751Notes

Reaction equation

C([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: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.[F:34][C:35]([F:40])([F:39])C(O)=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O>>[F:34][C:35]([F:40])([F:39])[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: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)[CH2:10][CH2:9]1)=[O:5]

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 9845Trifluoroacetic anhydride

HCID 532576834-[4-(4-Methanesulfonyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 579649212,2,2-Trifluoro-1-{4-[4-(4-methanesulfonyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidin-1-yl}-ethanone

Procedure

2,2,2-Trifluoro-1-{4-[4-(4-methanesulfonyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidin-1-yl}-ethanone was prepared according to General Procedure J 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, followed by reaction of the resulting amine with trifluoroacetic anhydride (available from Alfa Aesar, Ward Hill, Mass., USA). 1H NMR (400 MHz, DMSO-d6) δ 2.10-2.16 (m, 4H), 3.55-3.65 (m, 1H), 4.00-4.04 (m, 1H), 4.41-4.44 (m, 1H), 5.18-5.24 (m, 1H), 7.63-7.65 (m, 2H), 8.05-8.07 (m, 2H), 8.41 (s, 1H), 8.58 (s, 1H). Mass spectrum MH+=470.

Sources & evidence

ORD record: ord-e5c418738e0a4a4a99b90e66f803a164
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188098B2

Reaction notes

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