Triethylamine → HCID 57964908, compound

HRID 1931766Notes

Reaction equation

HRID 1931766 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[C:39]([CH:40]=O)=[CH:38][C:37]2[O:42][C:43]([F:46])([F:45])[O:44][C:36]=2[CH:35]=1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[F:46][C:43]1([F:45])[O:44][C:36]2[CH:35]=[CH:34][C:39]([CH2:40][N:29]3[CH2:28][CH2:27][CH:26]([N:23]4[C:19]5=[N:20][CH:21]=[N:22][C:17]([O:16][C:15]6[CH:14]=[CH:13][C:12]([S:9]([CH3:8])(=[O:11])=[O:10])=[CH:33][CH:32]=6)=[C:18]5[CH:25]=[N:24]4)[CH2:31][CH2:30]3)=[CH:38][C:37]=2[O:42]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27369732,2-Difluoro-5-formylbenzodioxoleHCID 5049666Sodium triacetoxyborohydrideHCID 669153264-(4-methanesulfonyl-phenoxy)-1-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidine trifluoroacetate salt2×

Product 1

HCID 57964908HCID 57964908, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

1-[1-(2,2-Difluoro-benzo[1,3]dioxol-5-ylmethyl)-piperidin-4-yl]-4-(4-methanesulfonyl-phenoxy)-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 2,2-difluoro-5-formylbenzodioxole (available from Aldrich Chemical Company, Inc., Milwaukee, Wis., USA), triethylamine, and sodium triacetoxyborohydride in 1,2-dichloroethane. 1H NMR (400 MHz, DMSO-d6) δ 1.89-1.98 (m, 2H), 2.15-2.25 (m, 4H), 2.92-2.98 (m, 2H), 3.30 (methyl sulfonyl and water peak), 3.57 (s, 2H), 4.77-4.83 (m, 1H), 7.18-7.20 (m, 1H), 7.35-7.39 (m, 2H), 7.62-7.64 (m, 2H), 8.04-8.07 (m, 2H), 8.37 (s, 1H), 8.55 (s, 1H). Mass spectrum MH+=544.

Sources & evidence

ORD record
ord-181c0017befe4770b597ee45c07341de
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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