Phenyl isocyanate → HCID 10251451, compound

HRID 1837582Notes

Reaction equation

HRID 1837582 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:18])[C:8]=2[N:7]=[C:6]1[CH2:19][CH2:20][O:21][CH3:22].[C:23]1([N:29]=[C:30]=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[NH2:18][C:9]1[C:8]2[N:7]=[C:6]([CH2:19][CH2:20][O:21][CH3:22])[N:5]([CH2:4][CH2:3][CH2:2][NH:1][C:30]([NH:29][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:31])[C:17]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1

Participants

3

Reactant 2

HCID 7672Phenyl isocyanateHCID 223444281-(3-aminopropyl)-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 10251451HCID 10251451, compoundYield 32%

Procedure

Using the general method of Example 149, 1-(3-aminopropyl)-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine (1.50 g, 5.01 mmol) was reacted with phenyl isocyanate (660 mg, 5.51 mmol). Recrystallization from acetonitrile provided 670 mg of N-(3-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propyl}-N′-phenylurea as light orange needles, m.p. ˜40° C. Analysis: Calculated for C23H26N6O2. 1.0 C2H3N: %C, 65.34; %H, 6.36; %N, 21.34; Found: %C, 65.13; %H, 6.26; %N, 21.35.

Workup

  1. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-e11f7f1c28e74f26bae6ab94df082b63
Source dataset
uspto-grants-2004_08
Patent number
US06784188B2

Reaction notes

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