Pivaloyl chloride → HCID 57965063, compound

HRID 1931742Notes

Reaction equation

HRID 1931742 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](Cl)(=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36]>>[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:34](=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36])[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 62493Pivaloyl chlorideHCID 669153264-(4-methanesulfonyl-phenoxy)-1-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidine trifluoroacetate salt2×

Product 1

HCID 57965063HCID 57965063, compound

Procedure

1-{4-[4-(4-Methanesulfonyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidin-1-yl}-2,2-dimethyl-propan-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 pivaloyl chloride (available from Aldrich Chemical Company, Inc., Milwaukee, Wis., USA). 1H NMR (400 MHz, DMSO-d6) δ 1.24 (s, 9H), 1.98-2.03 (m, 4H), 3.06-3.14 (m, 2H), 3.30 (methyl sulfonyl and water peak), 4.40-4.46 (m, 2H), 5.09-5.15 (m, 1H), 7.63-7.65 (m, 2H), 8.05-8.07 (m, 2H), 8.39 (s, 1H), 8.57 (s, 1H). Mass spectrum MH+=458.

Sources & evidence

ORD record
ord-4af56f9faa41442f87cad937fbc0f919
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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