Hydrazine hydrate (1:1) → HCID 67052370, compound

HRID 599462Notes

Reaction equation

HRID 599462 reaction equation
O.NN.[NH2:4][C:5]1[C:14]2[N:15]=[C:16]([CH2:28][O:29][N:30]3C(=O)C4C(=CC=CC=4)C3=O)[N:17]([CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:13]=2[C:12]2[CH:11]=[CH:10][C:9]([O:41][CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[CH:8][C:7]=2[N:6]=1>C(O)C>[NH2:4][C:5]1[C:14]2[N:15]=[C:16]([CH2:28][O:29][NH2:30])[N:17]([CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:26])[CH3:24])[C:13]=2[C:12]2[CH:11]=[CH:10][C:9]([O:41][CH2:42][C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)=[CH:8][C:7]=2[N:6]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67052505HCID 67052505, compound

Product 1

HCID 67052370HCID 67052370, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine hydrate (0.753 mL, 15.5 mmol) was added to a stirred suspension of tert-butyl 2-(4-amino-7-(benzyloxy)-2-{[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]methyl}-1H-imidazo[4,5-c]quinolin-1-yl)ethylcarbamate (3.15 g, 5.18 mmol) in ethanol (50 mL). The suspension was stirred at room temperature for 3 hours, then was filtered. The filtrate was concentrated under reduced pressure to yield 2.43 g of crude tert-butyl 2-[4-amino-2-[(aminooxy)methyl]-7-(benzyloxy)-1H-imidazo[4,5-c]quinolin-1-yl]ethylcarbamate that was used without purification in the next step.

Workup

  1. filtrationwas filtered
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-504533d6e6374fbe8d6c746f14cca566
Source dataset
uspto-grants-2011_03
Patent number
US07897767B2

Reaction notes

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