Triethylamine → HCID 19974262, compound

HRID 477089Notes

Reaction equation

HRID 477089 reaction equation
[C:1]([NH:9][C:10]1[S:11][CH:12]=[C:13]([C:15](=[O:18])[CH2:16]Br)[N:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]([NH:26][CH:27]([CH3:39])[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]([O:37][CH3:38])=[O:36])=[CH:31][CH:30]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C>CN(C)C=O>[C:35]([C:32]1[CH:33]=[CH:34][C:29]([CH2:28][CH:27]([N:26]([CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:16][CH:15]([OH:18])[C:13]2[N:14]=[C:10]([NH:9][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[S:11][CH:12]=2)[CH3:39])=[CH:30][CH:31]=1)([O:37][CH3:38])=[O:36]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 14076214HCID 14076214, compoundHCID 19974252HCID 19974252, compound

Product 1

HCID 19974262HCID 19974262, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3.5 g (0.011 mol) of 2-Benzoylamino-4-bromoacetyl-thiazole are dissolved in 20 ml of dimethylformamide and added dropwise to a stirred solution, at room temperature, of 2.6 g (0.092 mol) of N-benzyl-2-(4-carbomethoxyphenyl)-1-methylethylamine and 1.1 g (0.011 mol) of triethylamine dissolved in 40 ml of dimethylformamide. After 1.5 hours ice/water is added, and the mixture is extracted with methylene chloride. The extract is dried over sodium sulphate and concentrated. The resulting amino-ketone is taken up in 100 ml of methanol and at room temperature, 0.6 g of sodium borohydride is added. After 1 hour the mixture is evaporated to dryness, water is added, and hydrochloric acid is used to acidify. After 10 minutes the mixture is made alkaline with ammonia and extracted with methylene chloride. The extract is dried over sodium sulphate, concentrated and purified on a silica gel column using toluene/ethyl acetate=8:2 as eluant.

Workup

  1. extractionthe mixture is extracted with methylene chloride
  2. dry with materialThe extract is dried over sodium sulphate
  3. concentrationconcentrated
  4. customis taken up in 100 ml of methanol and at room temperature
  5. addition0.6 g of sodium borohydride is added
  6. customAfter 1 hour the mixture is evaporated to dryness, water
  7. additionis added
  8. extractionalkaline with ammonia and extracted with methylene chloride
  9. dry with materialThe extract is dried over sodium sulphate
  10. concentrationconcentrated
  11. custompurified on a silica gel column

Sources & evidence

ORD record
ord-31bdba4487384a97bc9d1f3224fe9e31
Source dataset
uspto-grants-1989_12
Patent number
US04886814

Reaction notes

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