Methyl bromoacetate → HCID 18384980, compound

HRID 395359Notes

Reaction equation

HRID 395359 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][NH:17][C:18]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]#[N:28])[CH:22]=2)=[O:19])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:29][CH2:30][C:31]([O:33][CH3:34])=[O:32]>CC(C)=O>[Br-:29].[CH2:1]([CH:8]1[CH2:9][CH2:10][N+:11]([CH2:30][C:31]([O:33][CH3:34])=[O:32])([CH2:14][CH2:15][CH2:16][NH:17][C:18]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]#[N:28])[CH:22]=2)=[O:19])[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 60984Methyl bromoacetateHCID 9842640HCID 9842640, compound

Product 1

HCID 18384980HCID 18384980, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-benzyl-1-[3-(3-cyanophenylaminocarbonylamino)prop-1-yl]piperidine (50 mg, 0.133 mmol, 1 eq), was dissoved in acetone at 25° C. under N2 then methyl bromoacetate (13 μL, 0.133 mmol, 1 eq),was added. After 16 hours, the solvent was removed in vacuo and the residue was purified over silica gel in 100% EtOAc to 8:2 chloroform/MeOH to yield 50 mg of white solids as product. NMR (300MHz, CD3OD) δ 8.00-7.80 (m, 1H); 7.65-7.45 (m, 1H); 7.45-7.33 (m, 1H); 7.33-7.05 (m, 6H); 4.50-4.25 (m, 2H); 4.00-3.60 (m, 5H); 3.50-3.20 (m, 6H); 2.70-2.50 (m, 2H); 2.10-1.60 (m, 7H).

Workup

  1. customthe solvent was removed in vacuo
  2. customthe residue was purified over silica gel in 100% EtOAc to 8:2 chloroform/MeOH

Sources & evidence

ORD record
ord-fd8645b334dc4baeae2ca25947afc9fc
Source dataset
uspto-grants-2003_08
Patent number
US06605623B1

Reaction notes

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