Methyl chloroformate → Ethyl 4-({4-[({6-[cyclohexyl(cyclopropylmethyl)amino]pyrimidin-4-yl}carbonyl)amino]phenyl}sulfonyl)butanoate

HRID 1746794노트

반응식

HRID 1746794 반응식
[CH:1]1([N:7]([CH2:17][CH:18]2[CH2:20][CH2:19]2)[C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([OH:16])=O)[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(NC(C)C)(C)C.ClC(OC)=O.[NH2:33][C:34]1[CH:39]=[CH:38][C:37]([S:40]([CH2:43][CH2:44][CH2:45][C:46]([O:48][CH2:49][CH3:50])=[O:47])(=[O:42])=[O:41])=[CH:36][CH:35]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH:1]1([N:7]([CH2:17][CH:18]2[CH2:20][CH2:19]2)[C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([NH:33][C:34]3[CH:39]=[CH:38][C:37]([S:40]([CH2:43][CH2:44][CH2:45][C:46]([O:48][CH2:49][CH3:50])=[O:47])(=[O:42])=[O:41])=[CH:36][CH:35]=3)=[O:16])[CH:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

참가 물질

7

반응물 5

HCID 6586Methyl chloroformateHCID 7912DiisopropylamineHCID 516892Sodium BicarbonateHCID 594468416-[Cyclohexyl(cyclopropylmethyl)amino]pyrimidine-4-carboxylic acid2회HCID 59446984Ethyl 4-(4-aminophenylsulfonyl)butanoate2회

생성물 1

HCID 59447011Ethyl 4-({4-[({6-[cyclohexyl(cyclopropylmethyl)amino]pyrimidin-4-yl}carbonyl)amino]phenyl}sulfonyl)butanoate

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

A cooled (0° C.) solution of 6-(cyclohexyl(cyclopropylmethyl)amino)pyrimidine-4-carboxylic acid (Intermediate 13, 130 mg; 0.47 mmol) in DCM was treated with diisopropylamine (90 mL; 0.52 mmol) and methyl chloroformate (40 mL; 0.52 mmol). After stirring at 0° C. for 15 minutes, ethyl 4-(4-aminophenylsulfonyl)butanoate (Intermediate 48, 130 mg; 0.48 mmol) was added. After stirring at 0° C. for 30 minutes and RT for 1 hour, saturated sodium bicarbonate solution was added and the mixture stirred for 15 minutes. DCM was added and the layers separated. The organic extract was filtered through a hydrophobic frit and the solvent removed in vacuo. The residue was purified by column chromatography (silica) eluting with petroleum ether containing increasing amounts of EtOAc to give the title compound as a white solid.

후처리

  1. stirringAfter stirring at 0° C. for 30 minutes and RT for 1 hour
  2. stirringthe mixture stirred for 15 minutes
  3. customthe layers separated
  4. extractionThe organic extract
  5. filtrationwas filtered through a hydrophobic frit
  6. customthe solvent removed in vacuo
  7. customThe residue was purified by column chromatography (silica)
  8. washeluting with petroleum ether containing
  9. temperatureincreasing amounts of EtOAc

출처 및 근거

ORD 기록
ord-fd43833c6f374b53b00db34e190f1e32
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150519B2

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