Triethylamine → 1-methyl-2-[(2R)-2-methyl-4-(quinoline-2-carbonyl)-piperazin-1-yl]-1H-[4,4']bipyrimidinyl-6-one

HRID 1045693ノート

反応式

HRID 1045693 の反応式
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][N:10]=2)[N:4]=[C:3]1[N:15]1[CH2:20][CH2:19][NH:18][CH2:17][C@H:16]1[CH3:21].C(N(CC)CC)C.[N:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][C:30]=1[C:39](Cl)=[O:40]>ClCCl>[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][N:10]=2)[N:4]=[C:3]1[N:15]1[CH2:20][CH2:19][N:18]([C:39]([C:30]2[CH:31]=[CH:32][C:33]3[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=3)[N:29]=2)=[O:40])[CH2:17][C@H:16]1[CH3:21]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 2760547Quinaldoyl chlorideHCID 250045961-methyl-2-((2R)-2-methyl-piperazin-1-yl)-1H-[4,4']bipyrimidinyl-6-one

生成物 1

HCID 578699251-methyl-2-[(2R)-2-methyl-4-(quinoline-2-carbonyl)-piperazin-1-yl]-1H-[4,4']bipyrimidinyl-6-one収率 78.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 1-methyl-2-((2R)-2-methyl-piperazin-1-yl)-1H-[4,4′]bipyrimidinyl-6-one (0.15 g, 0.52 mmol) and triethylamine (0.15 g, 1.48 mmol) in dichloromethane (2.5 ml) was added quinoline-2-carbonyl chloride (0.11 g, 0.57 mmol) at 0° C. and stirred for one hour at that temperature. The mixture was partitioned between water and dichloromethane, and the organic layer was washed with aqueous sodium hydrogen carbonate, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; chloroform/methanol=20/1) to afford 1-methyl-2-[(2R)-2-methyl-4-(quinoline-2-carbonyl)-piperazin-1-yl]-1H-[4,4′]bipyrimidinyl-6-one (0.18 g, 77%).

後処理

  1. customThe mixture was partitioned between water and dichloromethane
  2. washthe organic layer was washed with aqueous sodium hydrogen carbonate
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent; chloroform/methanol=20/1)

出典と根拠

ORDレコード
ord-ac6c7d5a3974485b841978943c11b74a
出典データセット
uspto-grants-2013_10
特許番号
US08569294B2

反応ノート

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