3,5-Dichlorobenzoyl chloride → HCID 57964881, compound

HRID 1931753Notes

Reaction equation

HRID 1931753 reaction equation
FC(F)(F)C(O)=O.[CH3:8][S:9]([C:12]1[CH:33]=[CH:32][C:15]([O:16][C:17]2[N:22]=[CH:21][N:20]=[C:19]3[N:23]([CH:26]4[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]4)[N:24]=[CH:25][C:18]=23)=[CH:14][CH:13]=1)(=[O:11])=[O:10].[Cl:34][C:35]1[CH:36]=[C:37]([CH:41]=[C:42]([Cl:44])[CH:43]=1)[C:38](Cl)=[O:39]>>[Cl:34][C:35]1[CH:36]=[C:37]([C:38]([N:29]2[CH2:28][CH2:27][CH:26]([N:23]3[C:19]4=[N:20][CH:21]=[N:22][C:17]([O:16][C:15]5[CH:14]=[CH:13][C:12]([S:9]([CH3:8])(=[O:11])=[O:10])=[CH:33][CH:32]=5)=[C:18]4[CH:25]=[N:24]3)[CH2:31][CH2:30]2)=[O:39])[CH:41]=[C:42]([Cl:44])[CH:43]=1

Participants

3

Reactant 2

HCID 761913,5-Dichlorobenzoyl chlorideHCID 669153264-(4-methanesulfonyl-phenoxy)-1-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidine trifluoroacetate salt2×

Product 1

HCID 57964881HCID 57964881, compound

Procedure

(3,5-Dichloro-phenyl)-{4-[4-(4-methanesulfonyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidin-1-yl}-methanone was prepared according to General Procedure H by the reaction of 4-(4-methanesulfonyl-phenoxy)-1-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidine trifluoroacetate salt (Intermediate 27) with 3,5-dichlorobenzoyl chloride (available from Aldrich Chemical Company, Inc., Milwaukee, Wis., USA). 1H NMR (400 MHz, DMSO-d6) δ 2.02-2.10 (m, 4H), 3.12-3.18 (m, 1H), 3.30 (methyl sulfonyl and water peak), 3.62-3.68 (m, 1H), 4.54-4.60 (m, 1H), 5.10-5.16 (m, 1H), 7.54-7.55 (m, 2H), 7.63-7.65 (m, 2H), 7.72-7.73 (m, 1H), 8.05-8.07 (m, 2H), 8.41 (s, 1H), 8.58 (s, 1H). Mass spectrum MH+=546, M+Na=478.

Sources & evidence

ORD record
ord-73d499407d714579a7736b57b0d31c9a
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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