4-Toluenesulfonyl chloride → HCID 57447038, compound

HRID 2366635Notes

Reaction equation

HRID 2366635 reaction equation
[CH3:1][NH:2][C:3](=[O:22])[CH2:4][CH2:5][N:6]1[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:8]=[C:7]1[CH2:19][CH2:20][CH3:21].C1C=C(Cl)C=C(C(OO)=O)C=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[OH-].[NH4+:46]>>[NH2:46][C:10]1[C:9]2[N:8]=[C:7]([CH2:19][CH2:20][CH3:21])[N:6]([CH2:5][CH2:4][C:3]([NH:2][CH3:1])=[O:22])[C:18]=2[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:11]=1

Participants

5

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 69506742HCID 69506742, compound

Product 1

HCID 57447038HCID 57447038, compound

Procedure

N-Methyl-3-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)propanamide (4.7 g, 13 mmol) was treated with mCPBA (6.58 g, 38.2 mmol) followed by ammonium hydroxide (40 mL) and p-toluenesulfonyl chloride (3.27 g, 17.2 mmol) according to the method described in Part D of Example 8. The crude product was purified as described in Part D of Example 8 to provide 0.674 g of 3-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)-N-methylpropanamide as a tan powder, mp 177-178° C.

Workup

  1. customThe crude product was purified

Sources & evidence

ORD record
ord-1f5ceba34acc41f1ae618dcc12248a17
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

Loading…