2-tert-Butyl-1,3-diisopropylisourea → 4-(4-Bromo-2-chlorophenylamino)-6-chloronicotinic acid tert-butyl ester

HRID 494710

反応式

HRID 494710 の反応式
[C:1](OC(=NC(C)C)NC(C)C)([CH3:4])([CH3:3])[CH3:2].Cl.[Br:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]2[C:29]([C:30]([OH:32])=[O:31])=[CH:28][N:27]=[C:26]([Cl:33])[CH:25]=2)=[C:19]([Cl:34])[CH:18]=1>C1COCC1.CCOC(C)=O>[C:1]([O:31][C:30](=[O:32])[C:29]1[C:24]([NH:23][C:20]2[CH:21]=[CH:22][C:17]([Br:16])=[CH:18][C:19]=2[Cl:34])=[CH:25][C:26]([Cl:33])=[N:27][CH:28]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 2

HCID 110417822-tert-Butyl-1,3-diisopropylisoureaHCID 865967774-(4-Bromo-2-chlorophenylamino)-6-chloronicotinic acid hydrochloride salt

生成物 1

HCID 865967784-(4-Bromo-2-chlorophenylamino)-6-chloronicotinic acid tert-butyl ester収率 107.3%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

2-tert-Butyl-1,3-diisopropylisourea (8.04 g, 40.1 mmol) was added to a mixture of 4-(4-bromo-2-chlorophenylamino)-6-chloronicotinic acid hydrochloride salt (24) (2.91 g, 7.31 mmol) in THF (165 mL). After stirring for 2 hours at room temperature and 30 minutes at reflux, the reaction mixture was cooled to room temperature and diluted with EtOAc. The organic layer was washed with 10% K2CO3 and brine, dried (Na2SO4) and concentrated. The resulting residue was dissolved in CH2Cl2 and filtered. The filtrate was concentrated and purified by flash column chromatography using the Biotage system (CH2Cl2) to give the desired product (40) (3.28 g, 78%).

後処理

  1. temperatureat reflux
  2. temperaturethe reaction mixture was cooled to room temperature
  3. washThe organic layer was washed with 10% K2CO3 and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. dissolutionThe resulting residue was dissolved in CH2Cl2
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated
  9. custompurified by flash column chromatography

出典と根拠

ORDレコード
ord-b9925329c8134f9fbab4bddce9e963e1
出典データセット
uspto-grants-2009_05
特許番号
US07538120B2

関連ノート

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