Cesium carbonate → 8-(3-Chloropropoxy)-4-(2,4-dichloro-5-methoxyphenylamino)-7-methoxybenzo[g]quinoline-3-carbonitrile

HRID 902425노트

반응식

HRID 902425 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH3:10])=[CH:4][C:3]=1[NH:11][C:12]1[C:21]2[C:16](=[CH:17][C:18]3[CH:25]=[C:24]([OH:26])[C:23]([O:27][CH3:28])=[CH:22][C:19]=3[CH:20]=2)[N:15]=[CH:14][C:13]=1[C:29]#[N:30].C1(C)C=CC(S(O[CH2:41][CH2:42][CH2:43][Cl:44])(=O)=O)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[Cl:44][CH2:43][CH2:42][CH2:41][O:26][C:24]1[C:23]([O:27][CH3:28])=[CH:22][C:19]2[CH:20]=[C:21]3[C:16](=[CH:17][C:18]=2[CH:25]=1)[N:15]=[CH:14][C:13]([C:29]#[N:30])=[C:12]3[NH:11][C:3]1[CH:4]=[C:5]([O:9][CH3:10])[C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1]

참가 물질

5

반응물 3

HCID 10796Cesium carbonate2회HCID 694343-Chloropropyl p-toluenesulfonate2회HCID 178486403HCID 178486403, 화합물

생성물 1

HCID 101425988-(3-Chloropropoxy)-4-(2,4-dichloro-5-methoxyphenylamino)-7-methoxybenzo[g]quinoline-3-carbonitrile수율 23.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Following the procedure of Example 16, 0.43 g (0.98 mmol) of 4-(2,4-dichloro-5-methoxyphenylamino)-8-hydroxy-7-methoxybenzo[g]quinoline-3-carbonitrile is reacted with 0.31 g (1.25 mmol) of 3-chloropropyl p-toluene sulfonate and 0.48 g of (1.47 mmol) of cesium carbonate, then an additional 0.05 g (0.2 mmol) of 3-chloropropyl p-toluene sulfonate and 0.07 g (0.2 mmol) of cesium carbonate in 6 mL of dry dimethyl formamide. The crude product is purified by silica gel flash chromatography, utilizing a 99.5:0.5 to 99:1 gradient of methylene chloride/methanol to give 0.118 g of 8-(3-chloropropoxy)-4-(2,4-dichloro-5-methoxyphenylamino)-7-methoxybenzo[g]quinoline-3-carbonitrile as a yellow solid, mp 220-223° C.

후처리

  1. customThe crude product is purified by silica gel flash chromatography

출처 및 근거

ORD 기록
ord-762b858f7fb24fc7b97864f59040f7e2
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07365197B2

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