Triethylamine → HCID 58833658, compound

HRID 2203578Notes

Reaction equation

HRID 2203578 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-09ff7d643f2444e790f7ac3d1f33cd68
Source dataset
uspto-grants-2016_06
Patent number
US09365567B2

Reaction notes

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