4-Methylmorpholine → 1-(4-chlorophenyl)-N-(3-(4-(2,3-dichlorophenyl)piperazin-1-yl)-2-hydroxy propyl)-2-propyl-1H-imidazole-4-carboxamide

HRID 75487노트

반응식

HRID 75487 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([C:13]([OH:15])=O)[N:10]=[C:9]2[CH2:16][CH2:17][CH3:18])=[CH:4][CH:3]=1.[Li].Cl.Cl.[NH2:22][CH2:23][CH:24]([OH:40])[CH2:25][N:26]1[CH2:31][CH2:30][N:29]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[C:33]=2[Cl:39])[CH2:28][CH2:27]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[C:11]([C:13]([NH:22][CH2:23][CH:24]([OH:40])[CH2:25][N:26]3[CH2:27][CH2:28][N:29]([C:32]4[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[C:33]=4[Cl:39])[CH2:30][CH2:31]3)=[O:15])[N:10]=[C:9]2[CH2:16][CH2:17][CH3:18])=[CH:6][CH:7]=1

참가 물질

7

반응물 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 66899052lithium 1-(4-chlorophenyl)-2-propyl-1H-imidazole-4-carboxylic acid2회HCID 674957041-Amino-3-(4-(2,3-dichlorophenyl)piperazin-1-yl)propan-2-ol dihydrochloride2회

생성물 1

HCID 498693581-(4-chlorophenyl)-N-(3-(4-(2,3-dichlorophenyl)piperazin-1-yl)-2-hydroxy propyl)-2-propyl-1H-imidazole-4-carboxamide수율 24%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a mixture of lithium 1-(4-chlorophenyl)-2-propyl-1H-imidazole-4-carboxylic acid (compound 6, 150 mg, 0.57 mmol), 1-amino-3-(4-(2,3-dichlorophenyl)piperazin-1-yl)propan-2-ol dihydrochloride (compound 41, 260 mg, 0.68 mmol), EDCI (165 mg, 0.85 mmol) and HOBt (154 mg, 1.14 mmol) in anhydrous DMF (7 mL) was added NMM (190 μl, 1.71 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 (74 mg, 24%) as a white solid.

후처리

  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)

출처 및 근거

ORD 기록
ord-7b12b30d0a9748c9ae17fb83928193a7
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835436B2

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