Benzenesulfonyl chloride → HCID 58970355, compound

HRID 2366710Notes

Reaction equation

[CH3:1][N:2]([CH3:23])[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(S(Cl)(=O)=O)C=CC=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]([N:2]([CH3:1])[CH3:23])=[O:22])[C:18]=2[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:11]=1

Participants

Reactant 4

HCID 7369Benzenesulfonyl chloride

HCID 14923Ammonium Hydroxide

HCID 70297m-Chloroperbenzoic acid

HCID 57447094HCID 57447094, compound

Product 1

HCID 58970355HCID 58970355, compound

Procedure

N,N-Dimethyl-3-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)propanamide (2.40 g, 7.73 mmol) was treated with mCPBA (3.11 g, 13.5 mmol), ammonium hydroxide (40 mL), and benzenesulfonyl chloride (1.92 mL, 15.1 mmol) according to the method described in Part D of Example 36. The crude product was purified by column chromatography on silica gel (eluting with 93:7 dichloromethane:methanol) to provide 0.097 g of 3-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)-N,N-dimethylpropanamide as a tan powder, mp 207-209° C.

Workup

customThe crude product was purified by column chromatography on silica gel (eluting with 93:7 dichloromethane:methanol)

Sources & evidence

ORD record: ord-a54ef8e37d1c41eeb898ccda58db3bce
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697873B2

Reaction notes

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