Trifluoroacetic acid → HCID 57568679, compound

HRID 1845722Notes

Reaction equation

HRID 1845722 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C:9]1[C:18]2[N:19]=[C:20]([CH2:27][O:28][CH2:29][CH3:30])[N:21]([CH2:22][C:23]([OH:26])([CH3:25])[CH3:24])[C:17]=2[C:16]2[CH:15]=[CH:14][C:13]([O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][O:40][CH2:41][CH2:42][NH:43][C:44](=[O:67])[CH2:45][CH2:46][S:47]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:12][C:11]=2[N:10]=1.C([SiH](CC)CC)C>ClCCl>[NH2:8][C:9]1[C:18]2[N:19]=[C:20]([CH2:27][O:28][CH2:29][CH3:30])[N:21]([CH2:22][C:23]([OH:26])([CH3:25])[CH3:24])[C:17]=2[C:16]2[CH:15]=[CH:14][C:13]([O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][O:40][CH2:41][CH2:42][NH:43][C:44](=[O:67])[CH2:45][CH2:46][SH:47])=[CH:12][C:11]=2[N:10]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 68924304HCID 68924304, compound

Product 1

HCID 57568679HCID 57568679, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Trifluoroacetic acid (8 mL) was added to a 0° C. solution of N-(2-{2-[2-(2-{[4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]oxy}ethoxy)ethoxy]ethoxy}ethyl)-3-(tritylthio)propanamide (1.38 g, 1.65 mmol) and triethylsilane (3.16 mL, 19.8 mmol) in dichloromethane (12 mL). The solution was stirred at 0° C. for 2 hours, then was concentrated under reduced pressure. The residue was concentrated under reduced pressure from toluene several times. The crude product was purified twice by HPFC on silica gel (gradient elution with 2-70% CMA in chloroform) to provide 0.55 g of N-(2-{2-[2-(2-{[4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]oxy}ethoxy)ethoxy]ethoxy}ethyl)-3-mercaptopropanamide as a foam. MS (ESI) m/z 594 (M+H)+. Anal. Calcd for C28H43N5O7S: C, 56.64; H, 7.30; N, 11.80; S, 5.40. Found: C, 56.36; H, 7.52; N, 11.53; S, 5.34.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. concentrationThe residue was concentrated under reduced pressure from toluene several times
  3. customThe crude product was purified twice by HPFC on silica gel (gradient elution with 2-70% CMA in chloroform)

Sources & evidence

ORD record
ord-88a42d5a5c554f18a51bebfd23db9de9
Source dataset
uspto-grants-2015_02
Patent number
US08951528B2

Reaction notes

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