HCID 178468536, compound → HCID 178468535, compound

HRID 1526130Notes

Reaction equation

HRID 1526130 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([CH:20]3[C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:24]([C:31]4[C:36]([F:37])=[CH:35][CH:34]=[C:33]([F:38])[C:32]=4[F:39])[NH:23][C:22]4[NH:40][N:41]=[C:42]([C:43]5[S:44][CH:45]=[CH:46][CH:47]=5)[C:21]3=4)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>ClCCl.[O-2].[Mn+2]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][C:17]([C:20]3[C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:24]([C:31]4[C:36]([F:37])=[CH:35][CH:34]=[C:33]([F:38])[C:32]=4[F:39])[N:23]=[C:22]4[NH:40][N:41]=[C:42]([C:43]5[S:44][CH:45]=[CH:46][CH:47]=5)[C:21]=34)=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 178468536HCID 178468536, compound

Product 1

HCID 178468535HCID 178468535, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalystHCID 6344DichloromethaneSolvent

Procedure

254 mg (2.93 mmol) of manganese oxide is added to 300 mg (0.45 mmol) of ethyl 4-(4-(4-(tert-butoxycarbonyl)piperazin-1-yl)phenyl)-3-(thiophen-2-yl)-6-(2,3,6-trifluorophenyl)-4,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylate in solution in 10 ml of dichloromethane. The reaction mixture is placed in an ultrasonic bath for 5 minutes and then stirred at room temperature for 20 hours. It is then filtered on silica (eluent: 65:35 cyclohexane/ethyl acetate) to yield 254 mg (85%) of ethyl 4-(4-(4-(tert-butoxycarbonyl)piperazin-1-yl)phenyl)-3-(thiophen-2-yl)-6-(2,3,6-trifluorophenyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate in the form of a yellow solid.

Workup

  1. filtrationIt is then filtered on silica (eluent: 65:35 cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-1b6c80bb1287455a9f40cf13b97fd369
Source dataset
uspto-grants-2015_07
Patent number
US09085575B2

Reaction notes

Loading…