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

HRID 599398Notes

Reaction equation

HRID 599398 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-f6951c626aea4a8eb225ec76e4201f8a
Source dataset
uspto-grants-2011_03
Patent number
US07897767B2

Reaction notes

Loading…