4-Cyanophenol → HCID 57965002, compound

HRID 1931653Notes

Reaction equation

HRID 1931653 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].[C:24]([C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)#[N:25]>C(#N)C>[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:32][C:29]4[CH:30]=[CH:31][C:26]([C:24]#[N:25])=[CH:27][CH:28]=4)=[C:17]3[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 130194-CyanophenolHCID 57964905Tert-butyl 4-(4-chloro-1H-pyrazolo[3,4-D]pyrimidin-1-YL)piperidine-1-carboxylate2×

Product 1

HCID 57965002HCID 57965002, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-[4-(4-Cyano-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester was prepared according to General Procedure A by the reaction of 4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 19) with 4-cyanophenol (available from Aldrich Chemical Company, Inc., Milwaukee, Wis., USA) in acetonitrile. 1H NMR (400 MHz, DMSO-d6) δ 1.43 (s, 9H), 1.94-2.04 (m, 4H), 2.95-3.05 (m, 2H), 4.08-4.11 (m, 2H), 4.98-5.04 (m, 1H), 7.58-7.60 (m, 2H), 7.99-8.01 (m, 2H), 8.37 (s, 1H), 8.56 (s, 1H). Mass spectrum MH+=421.

Sources & evidence

ORD record
ord-f05d02c1af09435987dd82390ea546f0
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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