(4-Tert-butylbenzyl)-[2-(3,4-dichloro-phenyl)-ethyl]-amine → N-(4-tert-butylbenzyl)-2-chloro-N-[2-(3,4-dichlorophenyl)-ethyl]-3-fluoro-6-methylaminobenzamide

HRID 2244378노트

반응식

HRID 2244378 반응식
[Cl:1][C:2]1[C:11]2[C:10](=[O:12])OC(=O)[N:7]([CH3:14])[C:6]=2[CH:5]=[CH:4][C:3]=1[F:15].[C:16]([C:20]1[CH:37]=[CH:36][C:23]([CH2:24][NH:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([Cl:35])[CH:29]=2)=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17]>CN(C=O)C.C(OCC)(=O)C>[C:16]([C:20]1[CH:37]=[CH:36][C:23]([CH2:24][N:25]([CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([Cl:35])[CH:29]=2)[C:10](=[O:12])[C:11]2[C:6]([NH:7][CH3:14])=[CH:5][CH:4]=[C:3]([F:15])[C:2]=2[Cl:1])=[CH:22][CH:21]=1)([CH3:19])([CH3:17])[CH3:18]

참가 물질

5

반응물 2

HCID 68563688(4-Tert-butylbenzyl)-[2-(3,4-dichloro-phenyl)-ethyl]-amineHCID 866152375-chloro-6-fluoro-1-methyl-1H-benzo[d][1,3]oxazine-2,4-dione

생성물 1

HCID 68699593N-(4-tert-butylbenzyl)-2-chloro-N-[2-(3,4-dichlorophenyl)-ethyl]-3-fluoro-6-methylaminobenzamide수율 27.1%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
140 °C

실험 절차

A mixture of 5-chloro-6-fluoro-1-methyl-1H-benzo[d][1,3]oxazine-2,4-dione (83 mg, 0.36 mmol) and (4-tert-butylbenzyl)-[2-(3,4-dichloro-phenyl)-ethyl]-amine (122 mg, 0.36 mmol) in DMF (2 ml) was heated to 140° C. for 2 h and then at 110° C. overnight. The reaction mixture was then cooled to RT and the mixture was diluted with ethyl acetate and washed with water and brine. The organic layer was dried (MgSO4), filtered and concentrated in vacuo to give a residue which was purified by flash column chromatography to give the desired product (51 mg, 27%) as a white solid. MS (ISP) 521.9 (M+H)+.

후처리

  1. customat 110° C.
  2. customovernight
  3. temperatureThe reaction mixture was then cooled to RT
  4. washwashed with water and brine
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a residue which
  9. customwas purified by flash column chromatography

출처 및 근거

ORD 기록
ord-852e110b28ee4bfc94e3a55108dd8d44
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07678818B2

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