Ethyl bromoacetate → HCID 25062686, compound

HRID 331214Notes

Reaction equation

HRID 331214 reaction equation
[CH:1]1([N:11]2[CH2:16][CH2:15][CH:14]([N:17]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[NH:19][C:18]3=[O:26])[CH2:13][CH2:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Br[CH2:30][C:31]([O:33]CC)=O.[CH3:36][NH2:37].CO>O1CCCC1>[CH:1]1([N:11]2[CH2:16][CH2:15][CH:14]([N:17]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[N:19]([CH2:30][C:31]([NH:37][CH3:36])=[O:33])[C:18]3=[O:26])[CH2:13][CH2:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 57454252Monomethylamine methanolHCID 59322905HCID 59322905, compound

Product 1

HCID 25062686HCID 25062686, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

1-[1-(1,2,3,4-Tetrahydronaphthalen-1-yl)piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one (476 mg) was dissolved in tetrahydrofuran (5 ml), 60% sodium hydride (66 mg) was added, and the suspension was stirred at 50° C. for 30 min. After cooling to room temperature, ethyl bromoacetate (0.167 ml) was added, and the mixture was stirred for 1 hr. 40% Methylamine-methanol solution (5 ml) was added, the mixture was stirred at room temperature for 1 hr, and the reaction mixture was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform/methanol) to give the title compound (567 mg) as a pale-yellow powder.

Workup

  1. temperatureAfter cooling to room temperature
  2. stirringthe mixture was stirred for 1 hr
  3. stirringthe mixture was stirred at room temperature for 1 hr
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-ecc589e250c84f139819f8178e84c80c
Source dataset
uspto-grants-2014_11
Patent number
US08877779B2

Reaction notes

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