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Triethylamine → 6-[cyclohexyl(cyclopropylmethyl)amino]-N-[4-(4-methyl-4H-1,2,4-triazol-3-yl)phenyl]pyrimidine-4-carboxamide

HRID 1746799
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HRID 1746799 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(N(CC)CC)C.[CH3:28][N:29]1[CH:33]=[N:32][N:31]=[C:30]1[C:34]1[CH:40]=[CH:39][C:37]([NH2:38])=[CH:36][CH:35]=1>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:38][C:37]3[CH:36]=[CH:35][C:34]([C:30]4[N:29]([CH3:28])[CH:33]=[N:32][N:31]=4)=[CH:40][CH:39]=3)=[O:16])[CH:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 27947854-(4-Methyl-4H-1,2,4-Triazol-3-Yl)AnilineHCID 594468416-[Cyclohexyl(cyclopropylmethyl)amino]pyrimidine-4-carboxylic acid2회

생성물 1

HCID 594468776-[cyclohexyl(cyclopropylmethyl)amino]-N-[4-(4-methyl-4H-1,2,4-triazol-3-yl)phenyl]pyrimidine-4-carboxamide

시약·촉매·용매 1

HCID 6344Dichloromethane
용매

실험 절차

A solution of 6-(cyclohexyl(cyclopropylmethyl)amino)pyrimidine-4-carboxylic acid (Intermediate 13, 100 mg; 0.36 mmol) in DCM (4 ml) was treated with polymer-supported Mukaiyama reagent (400 mg) followed by triethylamine (100 mL; 0.73 mmol) and 4-(4-methyl-4H-1,2,4-triazol-3-yl)aniline (Maybridge, 63.2 mg; 0.36 mmol). After stirring at RT for 24 hours the mixture was filtered and washed with saturated sodium bicarbonate solution. The organic phase was passed 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. filtrationwas filtered
  2. washwashed with saturated sodium bicarbonate solution
  3. customthe solvent removed in vacuo
  4. customThe residue was purified by column chromatography (silica)
  5. washeluting with petroleum ether containing
  6. temperatureincreasing amounts of EtOAc

출처 및 근거

ORD 기록
ord-d6f68f6c73a741daa11836de90ccc4e2
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09150519B2

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