Triethylamine → HCID 15284162, compound

HRID 1654001Notes

Reaction equation

HRID 1654001 reaction equation
Br.[NH:2]([C:6]1[S:7][CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:10]=1)[C:3]([NH2:5])=[NH:4].C(N(CC)CC)C.[C:24]([N:27]1[CH2:32][CH2:31][C:30](=O)[CH:29]([C:34](=O)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:28]1)(=[O:26])[CH3:25].N(C1N=C(C2C=CC=CC=2)SC=1)C(N)=N>CC(C)=O>[C:24]([N:27]1[CH2:28][C:29]2[C:34]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[N:4][C:3]([NH:2][C:6]3[S:7][CH:8]=[C:9]([C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)[N:10]=3)=[N:5][C:30]=2[CH2:31][CH2:32]1)(=[O:26])[CH3:25]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10467041HCID 10467041, compoundHCID 178419715HCID 178419715, compoundHCID 178512593HCID 178512593, compound

Product 1

HCID 15284162HCID 15284162, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To 2-guanidino-4-phenylthiazole hydrobromide (13.14 g, 0.044 mol) was added acetone (240 mL), with stirring. Triethylamine (4.45 g, 6.3 mL, 0.044 mol) was added. The resulting solution was heterogeneous. N-Acetyl-3-benzoyl-4-piperidone (7.18 g, 0.029 mol) was dissolved in acetone (30 mL), with gentle warming, then added to the guanidino phenylthiazole solution. The reaction mixture was heated at reflux for three days. The solid which had precipitated was filtered in a sintered glass funnel, and washed with water to remove triethylamine hydrobromide. The remaining solid, composed of the desired product along with a small amount of the excess starting guanidino phenylthiazole, was recrystallized from methanol to give 3.29 g (7.7 mmol) of the title compound as a tan solid; mp 130°-132° C. A second crop precipitated from the mother liquor and was recrystallized from methanol to give an additional 2.7 g (6.3 mmol). The combined yield was 48%.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for three days
  3. customThe solid which had precipitated
  4. filtrationwas filtered in a sintered glass funnel
  5. washwashed with water
  6. customto remove triethylamine hydrobromide
  7. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-833e161edf9549fc891decd63d84186e
Source dataset
uspto-grants-1995_04
Patent number
US05405848

Reaction notes

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