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4-Methylmorpholine → N-(3-(4-(2,3-dichlorophenyl)piperazin-1-yl)-2-hydroxypropyl)-2,5-dimethyl-1-phenyl-1H-imidazole-4-carboxamide

HRID 75493
ノート
印刷プレビュー

反応式

HRID 75493 の反応式
[CH3:1][C:2]1[N:3]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:4]([CH3:10])=[C:5]([C:7]([O-:9])=O)[N:6]=1.[Li+].Cl.Cl.[NH2:20][CH2:21][CH:22]([OH:38])[CH2:23][N:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[C:31]=2[Cl:37])[CH2:26][CH2:25]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>CN(C=O)C>[Cl:37][C:31]1[C:32]([Cl:36])=[CH:33][CH:34]=[CH:35][C:30]=1[N:27]1[CH2:28][CH2:29][N:24]([CH2:23][CH:22]([OH:38])[CH2:21][NH:20][C:7]([C:5]2[N:6]=[C:2]([CH3:1])[N:3]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH3:10])=[O:9])[CH2:25][CH2:26]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 54579221Lithium 2,5-dimethyl-1-phenyl-1H-imidazole-4-carboxylate2 回HCID 674957041-Amino-3-(4-(2,3-dichlorophenyl)piperazin-1-yl)propan-2-ol dihydrochloride2 回

生成物 1

HCID 49869500
N-(3-(4-(2,3-dichlorophenyl)piperazin-1-yl)-2-hydroxypropyl)-2,5-dimethyl-1-phenyl-1H-imidazole-4-carboxamide
収率 40%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of lithium 2,5-dimethyl-1-phenyl-1H-imidazole-4-carboxylate (compound 13a, 150 mg, 0.67 mmol), 1-amino-3-(4-(2,3-dichlorophenyl)piperazin-1-yl)propan-2-ol dihydrochloride (compound 41, 300 mg, 0.80 mmol), EDCI (260 mg, 1.34 mmol) and HOBt (180 mg, 1.34 mmol) in anhydrous DMF (7 mL) was added NMM (370 μl, 3.35 mmol). The reaction mixture was stirred at room temperature for 15 hrs. The mixture was concentrated under reduced pressure. The residue was diluted with CH2Cl2, and washed with water. The organic layer was dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude product was purified by preparative HPLC (purification system, Gilson) to provide the title compound (134 mg, 40%) as a white solid.

後処理

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionThe residue was diluted with CH2Cl2
  3. washwashed with water
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by preparative HPLC (purification system, Gilson)

出典と根拠

ORDレコード
ord-c1e66017f68e45289719c1277abe6d52
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08835436B2

反応ノート

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