Trifluoroacetic acid → HCID 57964984, compound

HRID 1931610Notes

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]([NH:23][C:24]4[CH:29]=[C:28]([F:30])[C:27]([F:31])=[CH:26][C:25]=4[F:32])=[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]([NH:23][C:24]4[CH:29]=[C:28]([F:30])[C:27]([F:31])=[CH:26][C:25]=4[F:32])=[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 57965010HCID 57965010, compound

Product 1

HCID 57964984HCID 57964984, compound

Procedure

4-[4-(2,4,5-Trifluoro-phenylamino)-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-(2,4,5-trifluoro-phenylamino)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (Example 4) 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), 1.90-1.99 (m, 4H), 3.04-3.15 (m, 3H), 4.08-4.17 (m, 2H), 4.77-4.83 (m, 1H), 4.89-4.94 (m, 1H), 7.69-7.76 (m, 1H), 7.96-7.99 (m, 1H), 8.25 (m, 1H), 8.36 (s, 1H), 10.13 (s, 1H). Mass spectrum MH+=435.

Sources & evidence

ORD record: ord-8129fde22dfe4e489572238791662685
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188098B2

Reaction notes

Loading…