2,4-Dimethoxybenzylamine → 1-(4-{4-Cyano-3-[(2,4-dimethoxybenzyl)amino]isothiazol-5-yl}phenyl)-3-(2-fluoro-5-methylphenyl)urea

HRID 871004노트

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HRID 871004 반응식
Cl[C:2]1[C:6]([C:7]#[N:8])=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([NH:18][C:19]3[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:20]=3[F:26])=[O:17])=[CH:11][CH:10]=2)[S:4][N:3]=1.[CH3:27][O:28][C:29]1[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=[CH:33][C:30]=1[CH2:31][NH2:32]>C(Cl)Cl>[C:7]([C:6]1[C:2]([NH:32][CH2:31][C:30]2[CH:33]=[CH:34][C:35]([O:37][CH3:38])=[CH:36][C:29]=2[O:28][CH3:27])=[N:3][S:4][C:5]=1[C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([NH:18][C:19]2[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:20]=2[F:26])=[O:17])=[CH:11][CH:10]=1)#[N:8]

참가 물질

4

반응물 2

HCID 5972502,4-DimethoxybenzylamineHCID 866892241-[4-(3-Chloro-4-cyanoisothiazol-5-yl)phenyl]-3-(2-fluoro-5-methylphenyl)urea

생성물 1

HCID 866892251-(4-{4-Cyano-3-[(2,4-dimethoxybenzyl)amino]isothiazol-5-yl}phenyl)-3-(2-fluoro-5-methylphenyl)urea수율 21%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
73 °C

실험 절차

A suspension of 1-[4-(3-chloro-4-cyanoisothiazol-5-yl)phenyl]-3-(2-fluoro-5-methylphenyl)urea (4.3 g, 11.1 mmol) in 15 mL of 2,4-dimethoxybenzylamine was heated to 73° C. for 24 h. The reaction became clear after ˜3 h. The reaction was cooled to RT. The residue was diluted with 300 mL of DCM and was washed with 10% HCl solution two times, saturated Na2S2O5 two times followed by brine. The organic solution was dried with MgSO4, filtered, and concentrated. The crude product was purified by flash silica gel column eluted with 2-5% MTBE in DCM/hexanes (2:1) to obtain the title compound as a light yellow solid (1.19 g, 21%).

후처리

  1. temperatureThe reaction was cooled to RT
  2. washwas washed with 10% HCl solution two times, saturated Na2S2O5 two times
  3. dry with materialThe organic solution was dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by flash silica gel column
  7. washeluted with 2-5% MTBE in DCM/hexanes (2:1)

출처 및 근거

ORD 기록
ord-044bc3cb43a74d2ca08e601ee66cd699
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969583B2

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