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

HRID 564511

Reaction equation

HRID 564511 reaction equation
[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

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 18626912Dioxane methylene chlorideSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-c74673fe4ee440cc841d079512ed988e
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Linked notes

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