Benzenesulfonyl chloride → HCID 58970355、化合物

反応式

[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

参加物

反応物 4

HCID 7369Benzenesulfonyl chloride

HCID 14923Ammonium Hydroxide

HCID 70297m-Chloroperbenzoic acid

HCID 57447094HCID 57447094、化合物

生成物 1

HCID 58970355HCID 58970355、化合物

実験手順

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.

後処理

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

出典と根拠

ORDレコード: ord-a54ef8e37d1c41eeb898ccda58db3bce
出典データセット: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08697873B2

反応ノート

読み込み中…