Triethylamine → 4-fluorophenyl {2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}carbamate

HRID 18138

반응식

HRID 18138 반응식
[NH2:1][C:2]1[C:15]2[C:6](=[CH:7][C:8]3[C:9]4[C:14]=2[C:13](=[O:16])[N:12]([CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])[C:11](=[O:22])[C:10]=4[CH:23]=[CH:24][CH:25]=3)[CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:34]([O:36][C:37]1[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=1)=[O:35].C(Cl)Cl.CO>ClCCl>[CH3:21][N:19]([CH3:20])[CH2:18][CH2:17][N:12]1[C:11](=[O:22])[C:10]2[CH:23]=[CH:24][CH:25]=[C:8]3[C:9]=2[C:14](=[C:15]2[C:2]([NH:1][C:34](=[O:35])[O:36][C:37]4[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=4)=[CH:3][CH:4]=[CH:5][C:6]2=[CH:7]3)[C:13]1=[O:16]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 27332564-Fluorophenyl chloroformateHCID 1006541311-amino-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dioneHCID 21226129Dichloromethane methanol

생성물 1

HCID 167179354-fluorophenyl {2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}carbamate수율 72.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
20 °C

실험 절차

100 mg of 11-amino-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione (obtained in example 3) (0.30 mmol) were dissolved in 6 ml of dichloromethane. 85 μl (2 molar equivalents) of triethylamine and 105 mg (2 molar equivalents) of 4-fluorophenyl chloroformate were respectively added. The reaction mixture was maintained at 20° C. for 3 hours. The solvent was then evaporated under reduced pressure and the residue was submitted to a flash chromatography on silica, (eluent: CH2Cl2/methanol in a 95/5 volume ratio) to provide 103 mg (yield=66%) of the desired product (formula below) as an orange powder.

후처리

  1. customThe solvent was then evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-c94d88cca3d44cde873ed04a9b63fa98
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741337B2

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