3-(3,5-dichlorophenoxy)-1-({1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridine-3-yl}methyl)-4-(trifluoromethyl)pyridine-2(1H)-one → HCID 178507302, compound

HRID 1952376Notes

Reaction equation

HRID 1952376 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:46]=[C:47]([Cl:49])[CH:48]=1)[O:5][C:6]1[C:7](=[O:45])[N:8]([CH2:16][C:17]2[C:25]3[C:20](=[N:21][C:22]([NH:26]CC4C=CC(OC)=CC=4)=[CH:23][CH:24]=3)[N:19](CC3C=CC(OC)=CC=3)[N:18]=2)[CH:9]=[CH:10][C:11]=1[C:12]([F:15])([F:14])[F:13]>C(O)(C(F)(F)F)=O.C(OCC)(=O)C>[NH2:26][C:22]1[N:21]=[C:20]2[NH:19][N:18]=[C:17]([CH2:16][N:8]3[CH:9]=[CH:10][C:11]([C:12]([F:13])([F:14])[F:15])=[C:6]([O:5][C:4]4[CH:46]=[C:47]([Cl:49])[CH:48]=[C:2]([Cl:1])[CH:3]=4)[C:7]3=[O:45])[C:25]2=[CH:24][CH:23]=1

Participants

4

Reactant 1

HCID 595297743-(3,5-dichlorophenoxy)-1-({1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridine-3-yl}methyl)-4-(trifluoromethyl)pyridine-2(1H)-one

Product 1

HCID 178507302HCID 178507302, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(3,5-dichlorophenoxy)-1-({1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridine-3-yl}methyl)-4-(trifluoromethyl)pyridine-2(1H)-one (0.900 g, 12.7 mmol) dissolved in TFA (10 mL) was placed in an oil bath at 75° C. After 4 hours, the reaction mixture was diluted with ethyl acetate (100 mL), washed with 50% aqueous sodium carbonate (50 mL). The aqueous was back extracted with ethyl acetate (100 mL) and the combined organic extracts were dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The resulting solid was adsorbed onto silica gel and purified by column chromatography on a pre-packed silica gel Redi Sep 40 gram column, eluting with 0-5% methanol in CH2Cl2 to afford the title compound. 1H NMR (DMSO-d6) δ 12.60 (s, 1H), 8.00-7.90 (m, 1H), 7.65-7.50 (m, 1H), 7.40-7.30 (m, 1H), 7.12-7.00 (m, 2H), 6.65-6.55 (m, 1H), 6.42-6.25 (m, 3H), 5.40-5.30 (s, 2H). LRMS (M+1)=469.77.

Workup

  1. customwas placed in an oil bath at 75° C
  2. washwashed with 50% aqueous sodium carbonate (50 mL)
  3. extractionThe aqueous was back extracted with ethyl acetate (100 mL)
  4. dry with materialthe combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure
  7. custompurified by column chromatography on a pre-packed silica gel Redi Sep 40 gram column
  8. washeluting with 0-5% methanol in CH2Cl2

Sources & evidence

ORD record
ord-8b8e0478385143aeab652c2f86befef6
Source dataset
uspto-grants-2013_03
Patent number
US08404856B2

Reaction notes

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