Triethylamine → HCID 58833658, compound

HRID 540902Notes

Reaction equation

HRID 540902 reaction equation
[CH:1]([N:4]=[C:5]=[O:6])([CH3:3])[CH3:2].Cl.Cl.[NH2:9][C:10]1[C:19]2[N:20]=[C:21]([CH2:28][O:29][CH2:30][CH3:31])[N:22]([CH2:23][CH2:24][CH2:25][CH2:26][NH2:27])[C:18]=2[C:17]2[CH:16]=[CH:15][C:14]([O:32][CH2:33][CH2:34][CH2:35][N:36]3[CH2:40][CH2:39][CH2:38][C:37]3=[O:41])=[CH:13][C:12]=2[N:11]=1.C(N(CC)CC)C>ClCCl>[NH2:9][C:10]1[C:19]2[N:20]=[C:21]([CH2:28][O:29][CH2:30][CH3:31])[N:22]([CH2:23][CH2:24][CH2:25][CH2:26][NH:27][C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[O:6])[C:18]=2[C:17]2[CH:16]=[CH:15][C:14]([O:32][CH2:33][CH2:34][CH2:35][N:36]3[CH2:40][CH2:39][CH2:38][C:37]3=[O:41])=[CH:13][C:12]=2[N:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61277Isopropyl isocyanateHCID 68969163HCID 68969163, compound

Product 1

HCID 58833658HCID 58833658, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Isopropyl isocyanate (0.187 mL, 1.90 mmol) was added dropwise to a stirred solution of 1-(3-{[4-amino-1-(4-aminobutyl)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-7-yl]oxy}propyl)pyrrolidin-2-one dihydrochloride (prepared as described in Example 398, 1.0 g, 1.90 mmol) and triethylamine (0.530 mL, 3.80 mmol) in dichloromethane (20 mL) at room temperature. After 1.5 hours, the solvent was removed under reduced pressure and the residue was purified by flash chromatography (silica gel, gradient elution with 2-12% CMA in chloroform) followed by recrystallization from acetonitrile to yield 0.730 g of N-(4-{4-amino-2-(ethoxymethyl)-7-[3-(2-oxopyrrolidin-1-yl)propoxy]-1H-imidazo[4,5-c]quinolin-1-yl}butyl)-N′-isopropylurea as an opaque solid, mp 98-101° C.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customthe residue was purified by flash chromatography (silica gel, gradient elution with 2-12% CMA in chloroform)
  3. customfollowed by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-0a59ddb8d302403694d53ad8b6cd55fe
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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