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Diisopropylamine → Ethyl 4-(4-(6-((cyclopropyl methyl)(propyl)amino)pyrimidine-4-carboxamido)-3-methylphenylsulfonamido)butanoate

HRID 1746776
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HRID 1746776 반응식
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([S:17]([NH:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])(=[O:19])=[O:18])=[CH:13][C:12]=2[CH3:29])=[O:9])[CH:3]=1.C(NC(C)C)(C)C.[CH:37]1([CH2:40][NH:41][CH2:42][CH2:43][CH3:44])[CH2:39][CH2:38]1>C(O)C>[CH:37]1([CH2:40][N:41]([CH2:42][CH2:43][CH3:44])[C:2]2[N:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][C:11]3[CH:16]=[CH:15][C:14]([S:17]([NH:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])(=[O:19])=[O:18])=[CH:13][C:12]=3[CH3:29])=[O:9])[CH:3]=2)[CH2:39][CH2:38]1
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참가 물질

5

반응물 3

HCID 7912DiisopropylamineHCID 117787Cyclopropanemethanamine, N-propyl-HCID 59446961Ethyl 4-(4-(6-chloropyrimidine-4-carboxamido)-3-methylphenylsulfonamido)butanoate2회

생성물 1

HCID 67529174Ethyl 4-(4-(6-((cyclopropyl methyl)(propyl)amino)pyrimidine-4-carboxamido)-3-methylphenylsulfonamido)butanoate

시약·촉매·용매 1

HCID 702Ethanol
용매

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온도
160 °C

실험 절차

A solution of ethyl 4-(4-(6-chloropyrimidine-4-carboxamido)-3-methylphenylsulfonamido)butanoate (Intermediate 35, 123 mg; 0.31 mmol) and diisopropylamine (105.5 mL; 0.61 mmol) in ethanol (4 ml) was treated with N-(cyclopropylmethyl)propan-1-amine (45.3 mg; 0.4 mmol). The mixture was heated to 160° C. in a microwave for 1 hour and the solvent removed in vacuo. The residue purified by column chromatography (silica) eluting with petroleum ether containing increasing amounts of EtOAc to give ethyl 4-(4-(6-((cyclopropylmethyl)(propyl)amino)pyrimidine-4-carboxamido)-3-methylphenylsulfonamido)butanoate which was used directly without any further purification. The residue was dissolved in methanol (10 ml) and THF (10 ml) and treated with 5 N NaOH solution (1 ml). After stirring at RT for 5 hours the solvent was removed in vacuo. The residue was redissolved in water (10 ml) and acidified with conc. HCl. The aqueous phase was extracted with EtOAc and the organic extracts passed through a hydrophobic frit and the solvent removed in vacuo. The residue was triturated with petroleum ether to yield the title compound as a white solid.

후처리

  1. customthe solvent removed in vacuo
  2. customThe residue purified by column chromatography (silica)
  3. washeluting with petroleum ether containing
  4. temperatureincreasing amounts of EtOAc

출처 및 근거

ORD 기록
ord-025cbb0d20844b8dad2321a46a9f6363
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09150519B2

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