Triethylamine → HCID 57964917, compound

HRID 1931772Notes

Reaction equation

HRID 1931772 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].[S:34]1[CH:38]=[CH:37][N:36]=[C:35]1[CH:39]=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]([CH2:39][C:35]5[S:34][CH:38]=[CH:37][N:36]=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 27349031,3-Thiazole-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 669153264-(4-methanesulfonyl-phenoxy)-1-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidine trifluoroacetate salt2×

Product 1

HCID 57964917HCID 57964917, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

4-(4-Methanesulfonyl-phenoxy)-1-(1-thiazol-2-ylmethyl-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 25) with 2-thiazolecarboxaldehyde (available from Aldrich Chemical Company, Inc., Milwaukee, Wis., USA), triethylamine, and sodium triacetoxyborohydride in 1,2-dichloroethane. 1H NMR (400 MHz, DMSO-d6) δ 1.95-2.00 (m, 2H), 2.21-2.33 (m, 2H), 2.39-2.45 (m, 3H), 3.04-3.08 (m, 2H), 3.30 (methyl sulfonyl and water peak), 3.92 (s, 2H), 4.79-4.85 (m, 1H), 7.63-7.74 (m, 4H), 8.05-8.07 (m, 2H), 8.39 (s, 1H), 8.56 (s, 1H). Mass spectrum MH+=471.

Sources & evidence

ORD record
ord-186bbc6f86874cfd96f1ad7f1c0381f2
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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