4-Chloro-3-(trifluoromethyl)phenol → HCID 57964925, compound

HRID 1931662Notes

Reaction equation

HRID 1931662 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](Cl)=[C:17]3[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][C:26]=1[C:32]([F:35])([F:34])[F:33]>CN(C)C=O>[C: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:31][C:28]4[CH:29]=[CH:30][C:25]([Cl:24])=[C:26]([C:32]([F:35])([F:33])[F:34])[CH:27]=4)=[C:17]3[CH:16]=[N:15]2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 805204-Chloro-3-(trifluoromethyl)phenolHCID 57964905Tert-butyl 4-(4-chloro-1H-pyrazolo[3,4-D]pyrimidin-1-YL)piperidine-1-carboxylate2×

Product 1

HCID 57964925HCID 57964925, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[4-(4-Chloro-3-trifluoromethyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester was prepared according to General Procedure B by the reaction of 4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 19) with 2-chloro-5-hydroxybenzotrifluoride (available from Alfa Aesar, Ward Hill, Mass., USA) in dimethylformamide. 1H NMR (400 MHz, DMSO-d6) δ 1.43 (s, 9H), 1.96-2.05 (m, 4H), 2.96-3.04 (m, 2H), 4.08-4.11 (m, 2H), 4.99-5.04 (m, 1H), 7.73-7.76 (m, 1H), 7.86-7.89 (m, 1H), 7.96-7.98 (m, 1H), 8.41 (s, 1H), 8.58 (s, 1H). Mass spectrum MH+=498.

Sources & evidence

ORD record
ord-57352f6662884e33a6ad59ceece47246
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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