Potassium Carbonate → Methyl 5-((4-(4-(3-(cyclopropylmethyl)ureido)benzoyl)piperazin-1-yl)methyl)thiophene-2-carboxylate

HRID 408865Notes

Reaction equation

HRID 408865 reaction equation
[CH:1]1([CH2:4][NH:5][C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[O:16])=[CH:11][CH:10]=2)=[O:7])[CH2:3][CH2:2]1.Br[CH2:24][C:25]1[S:29][C:28]([C:30]([O:32][CH3:33])=[O:31])=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH:1]1([CH2:4][NH:5][C:6](=[O:7])[NH:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]([N:17]3[CH2:22][CH2:21][N:20]([CH2:24][C:25]4[S:29][C:28]([C:30]([O:32][CH3:33])=[O:31])=[CH:27][CH:26]=4)[CH2:19][CH2:18]3)=[O:16])=[CH:13][CH:14]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11424851Methyl 5-(bromomethyl)thiophene-2-carboxylateHCID 580558061-(Cyclopropylmethyl)-3-(4-(Piperazine-1-carbonyl)phenyl)urea

Product 1

HCID 58055790Methyl 5-((4-(4-(3-(cyclopropylmethyl)ureido)benzoyl)piperazin-1-yl)methyl)thiophene-2-carboxylateYield 90.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(Cyclopropylmethyl)-3-(4-(piperazine-1-carbonyl)phenyl)urea (4.25 mmol, 1.286 g), methyl 5-(bromomethyl)thiophene-2-carboxylate (4.25 mmol, 1 g) and potassium carbonate (12.76 mmol, 1.764 g) were stirred at room temperature in acetonitrile (20 mL) for 18 hours. The reaction mixture was concentrated at reduced pressure and the resulting residue taken up in dichloromethane, washed with water, dried over sodium sulfate and concentrated under vacuum to afford the title compound (1.764 g). MS (ESI) m/z 457.5 [M+H]+

Workup

  1. concentrationThe reaction mixture was concentrated at reduced pressure
  2. washwashed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-38fa9c596abb4d9cb99558d75d8a275a
Source dataset
uspto-grants-2014_06
Patent number
US08759352B2

Reaction notes

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