Cyclohexylacetyl chloride → 2-Cyclohexyl-1-{4-[4-(4-methanesulfonyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidin-1-yl}-ethanone

HRID 1931749Notes

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].[CH:34]1([CH2:40][C:41](Cl)=[O:42])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1>>[CH:34]1([CH2:40][C:41]([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:42])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

Reactant 2

HCID 2757989Cyclohexylacetyl chloride

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

Product 1

HCID 579650282-Cyclohexyl-1-{4-[4-(4-methanesulfonyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidin-1-yl}-ethanone

Procedure

2-Cyclohexyl-1-{4-[4-(4-methanesulfonyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidin-1-yl}-ethanone was prepared according to General Procedure I by the reaction of 4-(4-methanesulfonyl-phenoxy)-1-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidine trifluoroacetate salt (Intermediate 27) with cyclohexyl-acetyl chloride (available from Aldrich Chemical Company, Inc., Milwaukee, Wis., USA). 1H NMR (400 MHz, DMSO-d6) δ 0.90-0.98 (m, 2H), 1.05-1.19 (m, 4H), 1.65-1.78 (m, 7H), 1.95-2.09 (m, 5H), 2.25-2.27 (m, 2H), 2.79-2.85 (m, 1H), 3.30 (methyl sulfonyl and water peak), 4.04-4.08 (m, 1H), 4.54-4.58 (m, 1H), 5.06-5.11 (m, 1H), 7.63-7.65 (m, 2H), 8.05-8.07 (m, 2H), 8.40 (s, 1H), 8.57 (s, 1H). Mass spectrum MH+=498.5.

Sources & evidence

ORD record: ord-fdb62c573c344a22a90ca8c966743494
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188098B2

Reaction notes

Loading…