1,2-Dichloroethane → 1,1-Dimethylethyl 4-({5'-[({[3-(chloromethyl)phenyl]carbonyl}amino)methyl]-2'-fluoro-3-biphenylyl}methyl)-1-piperazinecarboxylate

HRID 564511

반응식

HRID 564511 반응식
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([F:29])=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]3)[CH:10]=2)[CH:8]=1.[Cl:30][CH2:31][C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][CH:40]=1)[C:35](O)=[O:36].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>O1CCOCC1.C(Cl)Cl>[Cl:30][CH2:31][C:32]1[CH:33]=[C:34]([C:35]([NH:1][CH2:2][C:3]2[CH:4]=[CH:5][C:6]([F:29])=[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]4[CH2:17][CH2:18][N:19]([C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[CH2:20][CH2:21]4)[CH:10]=3)[CH:8]=2)=[O:36])[CH:38]=[CH:39][CH:40]=1

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2417523-(Chloromethyl)benzoic acidHCID 578132811,1-Dimethylethyl 4-{[5'-(aminomethyl)-2'-fluoro-3-biphenylyl]methyl}-1-piperazinecarboxylate

생성물 1

HCID 578133491,1-Dimethylethyl 4-({5'-[({[3-(chloromethyl)phenyl]carbonyl}amino)methyl]-2'-fluoro-3-biphenylyl}methyl)-1-piperazinecarboxylate수율 49%

시약·촉매·용매 1

HCID 18626912Dioxane methylene chloride용매

실험 절차

To a solution of 1,1-dimethylethyl 4-{[5′-(aminomethyl)-2′-fluoro-3-biphenylyl]methyl}-1-piperazinecarboxylate (0.32 g, 0.80 mmol) in p-dioxane/DCM (4/4 mL) was added 3-(chloromethyl)benzoic acid (0.12 g, 0.88 mmol), EDC (0.23 g, 1.2 mmol), HOBt (0.011 g, 0.08 mmol), and Et3N (0.112 mL, 0.8 mmol). The mixture was stirred at room temperature for 50 min before was the reaction was quenched with H2O (3 mL). The organic layer was separated, dried over Na2SO4, filtered, concentrated and purified by CombiFlash chromatograph to afford the title compound 0.216 g (49%). LC-MS m/z 552 (M+H)+.

후처리

  1. customwas quenched with H2O (3 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by CombiFlash chromatograph

출처 및 근거

ORD 기록
ord-c74673fe4ee440cc841d079512ed988e
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067408B2

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