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

HRID 1746800ノート

反応式

HRID 1746800 の反応式
[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.[N:28]1([CH2:33][C:34]2[CH:40]=[CH:39][C:37]([NH2:38])=[CH:36][CH:35]=2)[CH:32]=[N:31][CH:30]=[N:29]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:39]=[CH:40][C:34]([CH2:33][N:28]4[CH:32]=[N:31][CH:30]=[N:29]4)=[CH:35][CH:36]=3)=[O:16])[CH:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 8212191-(4-Aminobenzyl)-1,2,4-triazoleHCID 594468416-[Cyclohexyl(cyclopropylmethyl)amino]pyrimidine-4-carboxylic acid2 回

生成物 1

HCID 594469666-[cyclohexyl(cyclopropylmethyl)amino]-N-[4-(1H-1,2,4-triazol-1-ylmethyl)phenyl]pyrimidine-4-carboxamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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-((1H-1,2,4-triazol-1-yl)methyl)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.

後処理

  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

出典と根拠

ORDレコード
ord-7addb6d3b1394479bb7ffd5d9405c49a
出典データセット
uspto-grants-2015_10
特許番号
US09150519B2

反応ノート

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