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

HRID 494710

반응식

HRID 494710 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-b9925329c8134f9fbab4bddce9e963e1
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538120B2

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