Triethylamine → 4-(4-Methanesulfonyl-phenoxy)-1-[1-(3-trifluoromethoxy-benzyl)-piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidine

HRID 1931765Notes

Reaction equation

HRID 1931765 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].[F:34][C:35]([F:46])([F:45])[O:36][C:37]1[CH:38]=[C:39]([CH:42]=[CH:43][CH:44]=1)[CH:40]=O.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:8][S:9]([C:12]1[CH:13]=[CH:14][C:15]([O:16][C:17]2[N:22]=[CH:21][N:20]=[C:19]3[N:23]([CH:26]4[CH2:27][CH2:28][N:29]([CH2:40][C:39]5[CH:42]=[CH:43][CH:44]=[C:37]([O:36][C:35]([F:34])([F:45])[F:46])[CH:38]=5)[CH2:30][CH2:31]4)[N:24]=[CH:25][C:18]=23)=[CH:32][CH:33]=1)(=[O:11])=[O:10]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 6051393-(Trifluoromethoxy)benzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 669153264-(4-methanesulfonyl-phenoxy)-1-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidine trifluoroacetate salt2×

Product 1

HCID 579649034-(4-Methanesulfonyl-phenoxy)-1-[1-(3-trifluoromethoxy-benzyl)-piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

4-(4-Methanesulfonyl-phenoxy)-1-[1-(3-trifluoromethoxy-benzyl)-piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidine 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-(trifluoromethoxy)benzaldehyde (available from Aldrich Chemical Company, Inc., Milwaukee, Wis., USA), triethylamine, and sodium triacetoxyborohydride in 1,2-dichloroethane. 1H NMR (400 MHz, DMSO-d6) δ 1.95-1.99 (m, 2H), 2.21-2.28 (m, 4H), 2.92-2.98 (m, 2H), 3.30 (methyl sulfonyl and water peak), 3.62 (s, 2H), 4.77-4.83 (m, 1H), 7.25-7.51 (m, 4H), 7.62-7.64 (m, 2H), 8.04-8.07 (m, 2H), 8.38 (s, 1H), 8.56 (s, 1H). Mass spectrum MH+=548.

Sources & evidence

ORD record
ord-8d535f1a9c444218a5f9468855fb5eed
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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