3,3-Dimethylbutanoyl chloride → HCID 57964931, compound

HRID 1931748Notes

Reaction equation

HRID 1931748 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].[C:34]([CH2:38][C:39](Cl)=[O:40])([CH3:37])([CH3:36])[CH3:35]>>[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]([C:39](=[O:40])[CH2:38][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:30][CH2:31]4)[N:24]=[CH:25][C:18]=23)=[CH:32][CH:33]=1)(=[O:11])=[O:10]

Participants

3

Reactant 2

HCID 815143,3-Dimethylbutanoyl chlorideHCID 669153264-(4-methanesulfonyl-phenoxy)-1-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidine trifluoroacetate salt2×

Product 1

HCID 57964931HCID 57964931, compound

Procedure

1-{4-[4-(4-Methanesulfonyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidin-1-yl}-3,3-dimethyl-butan-1-one 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 tert-butylacetyl chloride (available from Aldrich Chemical Company, Inc., Milwaukee, Wis., USA). 1H NMR (400 MHz, DMSO-d6) δ 1.02 (s, 9H), 1.93-2.06 (m, 4H), 2.30-2.35 (m, 2H), 2.79-2.84 (m, 1H), 3.30 (methyl sulfonyl and water peak), 4.14-4.17 (m, 1H), 4.59-4.62 (m, 1H), 5.05-5.11 (m, 1H), 7.63-7.65 (m, 2H), 8.05-8.07 (m, 2H), 8.38 (s, 1H), 8.57 (s, 1H). Mass spectrum MH+=472, M+Na=493.9.

Sources & evidence

ORD record
ord-2530b9914fdd4e62b12aa9b7dad1c498
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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