Acetic Acid → HCID 136338238, compound

HRID 1526115Notes

Reaction equation

HRID 1526115 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)=[C:8]([C:20](OCC)=[O:21])[C:9]=2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N+:17]([O-])=O)[NH:4][N:3]=1.[C:33](O)(=[O:35])[CH3:34]>[Fe]>[CH3:32][O:31][C:28]1[CH:29]=[CH:30][C:25]([C:7]2[C:8]3[C:20](=[O:21])[NH:17][C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=4[C:9]=3[C:10]3[C:2]([NH:1][C:33](=[O:35])[CH3:34])=[N:3][NH:4][C:5]=3[N:6]=2)=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 178468518HCID 178468518, compound

Product 1

HCID 136338238HCID 136338238, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

55 mg (1 mmol) of iron is added to a solution of 87 mg (0.2 mmol) of ethyl 3-amino-6-(4-methoxyphenyl)-4-(2-nitrophenyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate dissolved in 2 ml of acetic acid. The reaction medium is carried at 90° C. for 5 hours, and then the precipitate obtained is filtered on Dicalite and rinsed with a 98:2 dichloroethane/methanol mixture. The filtrate is concentrated to yield 45 mg (56%) of N-(5-(4-methoxyphenyl)-6-oxo-6,7-dihydro-3H-benzo[f]pyrazolo[3,4-c][2,7]naphthyridin-1-yl)acetamide in the form of a yellow solid.

Workup

  1. customthe precipitate obtained
  2. filtrationis filtered on Dicalite
  3. washrinsed with a 98:2 dichloroethane/methanol mixture
  4. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-54a4235842e54bc588d16806e9716f80
Source dataset
uspto-grants-2015_07
Patent number
US09085575B2

Reaction notes

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