Trifluoroacetic acid → HCID 57568677, compound

HRID 1845732Notes

Reaction equation

HRID 1845732 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:10][CH2:11][C:12]1[N:13]([CH2:25][C:26]([NH:29][C:30](=[O:44])[CH2:31][CH2:32][C:33]([NH:35][NH:36]C(OC(C)(C)C)=O)=[O:34])([CH3:28])[CH3:27])[C:14]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:17]=[CH:16][C:15]=2[N:24]=1)[CH3:9]>ClCCl>[CH2:8]([O:10][CH2:11][C:12]1[N:13]([CH2:25][C:26]([NH:29][C:30](=[O:44])[CH2:31][CH2:32][C:33]([NH:35][NH2:36])=[O:34])([CH3:28])[CH3:27])[C:14]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:17]=[CH:16][C:15]=2[N:24]=1)[CH3:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68926515HCID 68926515, compound

Product 1

HCID 57568677HCID 57568677, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (3 mL) was added slowly to a solution of tert-butyl 2-[4-({2-[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}amino)-4-oxobutanoyl]hydrazinecarboxylate (0.688 g, 1.34 mmol) in dichloromethane (7 mL). The solution was stirred for 2.5 hours, then was concentrated under reduced pressure. The trifluoroacetic acid salt of N-{2-[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}-4-hydrazino-4-oxobutanamide was applied to anion exchange resins, which were eluted with pyridine in methanol to provide N-{2-[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}-4-hydrazino-4-oxobutanamide as a free base, which was purified by HPFC on silica gel (gradient elution, 2-50% CMA in chloroform). The appropriate fractions were concentrated under reduced pressure to yield a foam that was heated under vacuum to afford 0.31 g of N-{2-[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}-4-hydrazino-4-oxobutanamide as a glassy solid.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. washwere eluted with pyridine in methanol

Sources & evidence

ORD record
ord-dc07bbb86de943e6939b86963f51f148
Source dataset
uspto-grants-2015_02
Patent number
US08951528B2

Reaction notes

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