2-Fluoro-4-(methylsulphonyl)aniline → HCID 57544434, compound

HRID 1931609Notes

Reaction equation

HRID 1931609 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].[F:24][C:25]1[CH:31]=[C:30]([S:32]([CH3:35])(=[O:34])=[O:33])[CH:29]=[CH:28][C:26]=1[NH2:27]>>[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:27][C:26]4[CH:28]=[CH:29][C:30]([S:32]([CH3:35])(=[O:34])=[O:33])=[CH:31][C:25]=4[F:24])=[C:17]3[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 27833852-Fluoro-4-(methylsulphonyl)anilineHCID 57964905Tert-butyl 4-(4-chloro-1H-pyrazolo[3,4-D]pyrimidin-1-YL)piperidine-1-carboxylate2×

Product 1

HCID 57544434HCID 57544434, compound

Procedure

4-[4-(2-Fluoro-4-methanesulfonyl-phenylamino)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester was prepared according to General Procedure C 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-fluoro-4-(methylsulfonyl)aniline (available from Aldrich Chemical Company, Inc., Milwaukee, Wis., USA). 1H NMR (400 MHz, DMSO-d6) δ 1.43 (s, 9H), 1.90-2.00 (m, 4H), 2.95-3.05 (m, 2H), 3.30 (methyl sulfonyl and water peak), 4.03-4.09 (m, 2H), 4.90-4.93 (m, 1H), 7.79-7.81 (m, 1H), 7.88-7.91 (m, 1H), 8.21-8.24 (m, 1H), 8.40-8.42 (m, 2H), 10.36 (s, 1H). Mass spectrum MH+=491.

Sources & evidence

ORD record
ord-785d69717ff24ec797dfae54fa39f699
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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