Hydrazine hydrate (1:1) → HCID 86627649, compound

HRID 1907936Notes

Reaction equation

HRID 1907936 reaction equation
O.NN.[NH2:4][C:5]1[C:14]2[N:15]=[C:16]([CH2:29][O:30][N:31]3C(=O)C4C(=CC=CC=4)C3=O)[N:17]([CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:13]=2[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[N:6]=1>C(O)C>[C:24]([O:23][C:22](=[O:28])[NH:21][CH2:20][CH2:19][CH2:18][N:17]1[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[C:5]([NH2:4])[C:14]=2[N:15]=[C:16]1[CH2:29][O:30][NH2:31])([CH3:27])([CH3:25])[CH3:26]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86627647HCID 86627647, compound

Product 1

HCID 86627649HCID 86627649, compoundYield 114.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine hydrate (8 mL of 55%) was added to a suspension of tert-butyl (3-{4-amino-2-[(1,3-dioxo-1,3-dihydroisoindol-2-yl)oxymethyl]-1H-imidazo[4,5-c]quinolin-1-yl}propyl)carbamate (4.25 g, 8.23 mmol) in ethanol (70 mL). The reaction became homogeneous after about 2 minutes. A precipitate started forming after about 1 hour. After stirring at ambient temperature for a total of 2 hours the reaction mixture was filtered and the filter cake was washed with dichloromethane. The filtrate was concentrated under reduced pressure. The residue was azeotroped twice with toluene to provide 3.63 g of tert-butyl[3-(4-amino-2-aminooxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]carbamate as a white solid.

Workup

  1. customA precipitate started forming after about 1 hour
  2. filtrationwas filtered
  3. washthe filter cake was washed with dichloromethane
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was azeotroped twice with toluene

Sources & evidence

ORD record
ord-148be54774674789a27443aa67be5656
Source dataset
uspto-grants-2013_12
Patent number
US08598192B2

Reaction notes

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