Methanol → HCID 52943186, compound

HRID 1914743Notes

Reaction equation

HRID 1914743 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:28][C:29]([F:32])([F:31])[F:30])=[C:8]([NH:10][C:11]2[N:20]=[CH:19][C:18]3[CH2:17][CH2:16][C:15]4[C:21]([C:25]([NH2:27])=[O:26])=[N:22][N:23]([CH3:24])[C:14]=4[C:13]=3[N:12]=2)[CH:9]=1)([O-])=O.CO>O.[Fe]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:28][C:29]([F:30])([F:32])[F:31])=[C:8]([NH:10][C:11]2[N:20]=[CH:19][C:18]3[CH2:17][CH2:16][C:15]4[C:21]([C:25]([NH2:27])=[O:26])=[N:22][N:23]([CH3:24])[C:14]=4[C:13]=3[N:12]=2)[CH:9]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 68668523HCID 68668523, compound

Product 1

HCID 52943186HCID 52943186, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

To a suspension of 8-(5-nitro-2-trifluoromethoxy-phenylamino)-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide (630 mg, 1.4 mmol) in methanol (6 mL) ammonium chloride (240 mg, 4.3 mmol) in water (25 mL) and iron (397 mg, 7.4 mmol) were added. The mixture was heated under reflux for 3 hours until HPLC revealed the disappearance of the starting material. The solvent was removed and the crude was diluted with trifluoroethanol. Iron was removed and the filtrate was concentrated to give the final compound as a light brown solid in quantitative yield.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 hours until HPLC
  3. customThe solvent was removed
  4. additionthe crude was diluted with trifluoroethanol
  5. customIron was removed
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-c55e1292c1584024a7bd828ebe6090a4
Source dataset
uspto-grants-2013_12
Patent number
US08614220B2

Reaction notes

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