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

HRID 871004ノート

反応式

HRID 871004 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
73 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-044bc3cb43a74d2ca08e601ee66cd699
出典データセット
uspto-grants-2015_03
特許番号
US08969583B2

反応ノート

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