Trifluoroacetic acid → HCID 57965020, compound

HRID 1931624Notes

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]([O:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[C:17]3[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=[O:7])(C)([CH3:3])[CH3:2].FC(F)(F)C(O)=O.ClC(OC(C)C)=O>>[CH:1]([O:5][C: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][CH:27]=[CH:28][CH:29]=4)=[C:17]3[CH:16]=[N:15]2)[CH2:12][CH2:13]1)=[O:7])([CH3:3])[CH3:2]

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 7917Isopropyl chloroformate

HCID 57964899HCID 57964899, compound

Product 1

HCID 57965020HCID 57965020, compound

Procedure

4-(4-Phenoxy-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid isopropyl ester was prepared according to General Procedure D by the reaction of 4-(4-phenoxy-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (from Step 1) with trifluoroacetic acid, followed by reaction of the resulting amine with isopropyl chloroformate (available from Aldrich Chemical Company, Inc., Milwaukee, Wis., USA). 1H NMR (400 MHz, DMSO-d6) δ 1.20 (d, 6H, J=6.2 Hz), 1.94-2.03 (m, 4H), 3.00-3.12 (m, 2H), 4.08-4.15 (m, 2H), 4.78-4.82 (m, 1H), 5.00-5.02 (m, 1H), 7.32-7.38 (m, 3H), 7.49-7.53 (m, 2H), 8.11 (s, 1H), 8.54 (s, 1H). Mass spectrum MH+=382.

Sources & evidence

ORD record: ord-2ae3bba3515b4f41af0375ad0dfca57d
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188098B2

Reaction notes

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