2,2,2-Trichloroethyl chloroformate → HCID 57964893, compound

HRID 1931720Notes

Reaction equation

HRID 1931720 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].Cl[C:35]([O:37][CH2:38][C:39]([Cl:42])([Cl:41])[Cl:40])=[O:36]>>[Cl:40][C:39]([Cl:42])([Cl:41])[CH2:38][O:37][C:35]([N:29]1[CH2:28][CH2:27][CH:26]([N:23]2[C:19]3=[N:20][CH:21]=[N:22][C:17]([O:16][C:15]4[CH:14]=[CH:13][C:12]([S:9]([CH3:8])(=[O:11])=[O:10])=[CH:33][CH:32]=4)=[C:18]3[CH:25]=[N:24]2)[CH2:31][CH2:30]1)=[O:36]

Participants

3

Reactant 2

HCID 870632,2,2-Trichloroethyl chloroformateHCID 669153264-(4-methanesulfonyl-phenoxy)-1-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidine trifluoroacetate salt2×

Product 1

HCID 57964893HCID 57964893, compound

Procedure

4-[4-(4-Methanesulfonyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid 2,2,2-trichloro-ethyl ester was prepared according to General Procedure E by the reaction of 4-(4-methanesulfonyl-phenoxy)-1-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidine trifluoro-acetate salt (Intermediate 27) with 2,2,2-trichloroethyl chloroformate (available from Aldrich Chemical Company, Inc., Milwaukee, Wis., USA). 1H NMR (400 MHz, DMSO-d6) δ 1.96-2.08 (m, 4H), 3.30 (methyl sulfonyl and water peak), 4.11-4.20 (m, 2H), 4.86-4.89 (m, 2H), 5.05-5.10 (m, 1H), 7.59-7.62 (m, 2H), 8.03-8.05 (m, 2H), 8.36 (s, 1H), 8.54 (s, 1H). Mass spectrum MH+=548.

Sources & evidence

ORD record
ord-9467969716af48589f43925da7cc9a18
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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