Trifluoroacetic acid → HCID 178468516, compound

HRID 1526116Notes

Reaction equation

HRID 1526116 reaction equation
FC(F)(F)C(O)=O.C(OC([NH:18][CH2:19][CH2:20][C:21]1[C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:25]([C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)[N:24]=[C:23]2[NH:40][N:41]=[C:42]([CH3:43])[C:22]=12)=O)C1C=CC=CC=1>ClCCl>[NH2:18][CH2:19][CH2:20][C:21]1[C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:25]([C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)[N:24]=[C:23]2[NH:40][N:41]=[C:42]([CH3:43])[C:22]=12

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178468517HCID 178468517, compound

Product 1

HCID 178468516HCID 178468516, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8 mL of trifluoroacetic acid is added to a solution of 220 mg (0.45 mmol) of ethyl 4-(2-(benzyloxycarbonylamino)ethyl)-6-(4-methoxyphenyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate dissolved in 5 mL of dichloromethane. The reaction medium is stirred at room temperature for 3 hours and then quenched by addition of 1M soda until pH=8 is reached. The product is extracted with ethyl acetate. The organic phases are dried on magnesium sulfate and concentrated to yield ethyl 4-(2-aminoethyl)-6-(4-methoxyphenyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate in the form of a yellow oil. The latter is dissolved in 10 mL of anhydrous tetrahydrofurane before adding 15 mg of sodium hydride (60% dispersion in oil). The reaction medium is stirred at 25° C. for 48 hours. The product is extracted with ethyl acetate. The organic phases are dried on magnesium sulfate and concentrated to yield 123 mg (88%) of 5-(4-methoxyphenyl)-1-methyl-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-6(7H)-one in the form of a yellow oil.

Workup

  1. customquenched by addition of 1M soda until pH=8
  2. extractionThe product is extracted with ethyl acetate
  3. customThe organic phases are dried on magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-37d88fb280724f409a860392d5248f7b
Source dataset
uspto-grants-2015_07
Patent number
US09085575B2

Reaction notes

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