o-Toluenesulfonyl chloride → HCID 69507195, compound

HRID 1623209Notes

Reaction equation

HRID 1623209 reaction equation
[CH2:1]([C:4]1[N:5]([CH2:17][CH2:18][CH2:19][CH2:20][OH:21])[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:16]=1)[CH2:2][CH3:3].[OH-].[NH4+:23].C1(C)C(S(Cl)(=O)=O)=CC=CC=1>C(Cl)(Cl)Cl.ClCCl>[NH2:23][C:8]1[C:7]2[N:16]=[C:4]([CH2:1][CH2:2][CH3:3])[N:5]([CH2:17][CH2:18][CH2:19][CH2:20][OH:21])[C:6]=2[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:9]=1

Participants

6

Reactant 3

HCID 8623o-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 57455407HCID 57455407, compound

Product 1

HCID 69507195HCID 69507195, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

4-(2-Propyl-1H-imidazo[4,5-c]quinolin-1-yl)butan-1-ol (7.27 g, 25.7 mmol, which can be prepared using the method described in Example 43 Part A) was oxidized and then animated using a modification of the general method described in Example 4 Part H. The oxidation was run in chloroform in lieu of dichloromethane and the crude N-oxide was isolated prior to being dissolved in dichloromethane and treated with ammonium hydroxide and toluene sulfonyl chloride. 3.82 g of 4-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butan-1-ol was obtained.

Workup

  1. customthe crude N-oxide was isolated

Sources & evidence

ORD record
ord-84f46d8a963841f69b627195da28e681
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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