Triethylamine → HCID 67165786, compound

HRID 552330Notes

Reaction equation

HRID 552330 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:4]=1[C:5]([N:7]1[CH2:12][CH2:11][C:10](=O)[CH2:9][CH2:8]1)=[O:6].Cl.[NH2:21][C@H:22]([C:27]([NH2:29])=[O:28])[CH2:23][CH2:24][S:25][CH3:26].C(N(CC)CC)C>CCO>[CH3:1][O:2][C:3]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:4]=1[C:5]([N:7]1[CH2:12][CH2:11][C:10]2([NH:29][C:27](=[O:28])[C@H:22]([CH2:23][CH2:24][S:25][CH3:26])[NH:21]2)[CH2:9][CH2:8]1)=[O:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18531008(2S)-2-amino-4-(methylsulfanyl)butanamide hydrochlorideHCID 24695582HCID 24695582, compound

Product 1

HCID 67165786HCID 67165786, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-(2,4-dimethoxybenzoyl)piperidin-4-one (1.4 g, 5.1 mmol), (S)-methioninamide hydrochloride (950 mg, 5.1 mmol) and triethylamine (520 mg, 5.1 mmol) in EtOH (40 ml) was heated under reflux for 2.5 h and stirred at RT for a further 16 h. After removal of the solvent, water (25 ml) and CH2Cl2 (25 ml) were added to the residue and it was rendered basic using conc. sodium hydroxide solution. The aqueous phase was extracted with CH2Cl2 (3×20 ml) and the combined organic phases were dried over Na2SO4. After removal of the solvent and drying in vacuo, the product 8-(2,4-dimethoxybenzoyl)-3-(S)-(2-methylsulfanylethyl)-1,4,8-triazaspiro[4,5]decan-2-one was obtained in a yield of 1.9 g (95%).

Workup

  1. temperatureunder reflux for 2.5 h
  2. customAfter removal of the solvent, water (25 ml) and CH2Cl2 (25 ml)
  3. additionwere added to the residue and it
  4. extractionThe aqueous phase was extracted with CH2Cl2 (3×20 ml)
  5. dry with materialthe combined organic phases were dried over Na2SO4
  6. customAfter removal of the solvent
  7. customdrying in vacuo

Sources & evidence

ORD record
ord-db89d749cab048ac8f8e678926939213
Source dataset
uspto-grants-2011_05
Patent number
US07951815B2

Reaction notes

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