Pyridine → HCID 10004788, compound

HRID 1839079Notes

Reaction equation

N[CH:2]([CH3:29])[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][CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[CH3:30][S:31]([O:34]S(C)(=O)=O)(=O)=[O:32].[N:39]1C=CC=CC=1>>[NH2:18][C:9]1[C:8]2[N:7]=[C:6]([CH2:19][CH2:20][CH2:21][O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:5]([CH2:4][CH2:3][CH2:2][CH2:29][NH:39][S:31]([CH3:30])(=[O:34])=[O:32])[C:17]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1

Participants

Reactant 3

HCID 1049Pyridine

HCID 81560Methanesulfonic anhydride

HCID 22344427HCID 22344427, compound

Product 1

HCID 10004788HCID 10004788, compound

Procedure

Using the general method of Example 255, except that pyridine was used in place of acetonitrile, 1-(3-aminobutyl)-2-(3-phenoxypropyl)-1H-imidazo[4,5-c]quinolin-4-amine (2.00 g, 5.1 mmol) was reacted with an excess of methanesulfonic anhydride to provide 1.36 g of N-{4-[4-amino-2-(3-phenoxypropyl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}methanesulfonamide as a solid, m.p. 156.4-157.1° C. Analysis: Calculated for C24H29N5O3S: %C, 60.48; %H, 6.34; %N, 14.69; Found: %C, 60.75; %H, 6.36; %N, 14.31.

Sources & evidence

ORD record: ord-f752c103dc774c8e9753801a4ed389ed
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06677349B1

Reaction notes

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