Phosgene → {2'-[3-(4-Chloro-benzyl)-1-ethyl-ureidomethyl]-4'-fluoro-6-methoxy-biphenyl-3-yl}-acetic acid ethyl ester

HRID 563691노트

반응식

HRID 563691 반응식
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[CH2:21][NH:22][CH2:23][CH3:24])[C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)[CH3:2].C(N(C(C)C)CC)(C)C.[C:35](Cl)(Cl)=[O:36].[Cl:39][C:40]1[CH:47]=[CH:46][C:43]([CH2:44][NH2:45])=[CH:42][CH:41]=1>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[CH2:21][N:22]([CH2:23][CH3:24])[C:35]([NH:45][CH2:44][C:43]2[CH:46]=[CH:47][C:40]([Cl:39])=[CH:41][CH:42]=2)=[O:36])[C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)[CH3:2]

참가 물질

6

반응물 4

HCID 6371PhosgeneHCID 660364-ChlorobenzylamineHCID 81531DiisopropylethylamineHCID 58149135(2'-Ethylaminomethyl-4'-fluoro-6-methoxy-biphenyl-3-yl)-acetic acid ethyl ester

생성물 1

HCID 58149334{2'-[3-(4-Chloro-benzyl)-1-ethyl-ureidomethyl]-4'-fluoro-6-methoxy-biphenyl-3-yl}-acetic acid ethyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

(2′-Ethylaminomethyl-4′-fluoro-6-methoxy-biphenyl-3-yl)-acetic acid ethyl ester (0.172 g, 0.5 mmol) and diisopropylethylamine (0.43 mL, 2.5 mmol) were combined in CH2Cl2 (2.5 mL) and cooled to 0° C. Phosgene (20% in toluene; 0.40 mL, 0.75 mmol) was added, and the mixture was stirred for 1 hour. 4-Chlorobenzylamine (0.012 mL, 1.0 mmol) was added, and the reaction was stirred for 1 hour. The mixture was diluted with CH2Cl2 and washed with H2O. The organic layer was dried, filtered, and concentrated, and the residue was purified by preparative HPLC to give the title compound.

후처리

  1. stirringthe reaction was stirred for 1 hour
  2. washwashed with H2O
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-65351d7693b8491082d84776d4dff687
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067445B2

반응 노트

불러오는 중…