Ammonia → 5-Acetyl-8-amino-1-(1,3-benzodioxol-5-yl)-4,5-dihydro-1h-pyrazolo[4,3-c]quinoline-3-carboxamide acetate

HRID 1348923Notes

Reaction equation

HRID 1348923 reaction equation
[C:1]([N:4]1[C:13]2[CH:12]=[CH:11][C:10]([NH2:14])=[CH:9][C:8]=2[C:7]2[N:15]([C:23]3[CH:31]=[CH:30][C:26]4[O:27][CH2:28][O:29][C:25]=4[CH:24]=3)[N:16]=[C:17]([C:18]([O:20]CC)=[O:19])[C:6]=2[CH2:5]1)(=[O:3])[CH3:2].[NH3:32]>C(O)C>[C:18]([OH:20])(=[O:19])[CH3:17].[C:1]([N:4]1[C:13]2[CH:12]=[CH:11][C:10]([NH2:14])=[CH:9][C:8]=2[C:7]2[N:15]([C:23]3[CH:31]=[CH:30][C:26]4[O:27][CH2:28][O:29][C:25]=4[CH:24]=3)[N:16]=[C:17]([C:18]([NH2:32])=[O:20])[C:6]=2[CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 21092645ethyl 5-acetyl-8-amino-1-(1,3-benzodioxol-5-yl)-4,5-dihydro-1H-pyrazolo[4,3-c]quinoline-3-carboxylate

Product 1

HCID 101388555-Acetyl-8-amino-1-(1,3-benzodioxol-5-yl)-4,5-dihydro-1h-pyrazolo[4,3-c]quinoline-3-carboxamide acetateYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

The material of Step 5 (450 mg, 0.00094 mol) was dissolved in ethanol (10 mL) and NH3 (10 mL), and the resulting reaction mixture was heated to 120° C. and shaken for 20 hours at 600 psi. The reaction was then cooled and vented for 2 hours. The resulting solution was concentrated in vacuo to give the product as a brown glass. 340 mg (MW=391.38, 93% yield). LC/MS m/z=392.05 (m+1).

Workup

  1. temperatureThe reaction was then cooled
  2. waitvented for 2 hours
  3. concentrationThe resulting solution was concentrated in vacuo

Sources & evidence

ORD record
ord-7aef8dee30e047c495af187b3b0aa7d9
Source dataset
uspto-grants-2007_05
Patent number
US07211597B2

Reaction notes

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