Triethylamine → HCID 68433023, compound

HRID 1882093Notes

Reaction equation

HRID 1882093 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]([CH2:14][CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:10](=O)[CH:11]=[CH2:12])=[N:7][CH:8]=1.[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([CH:28]=O)=[N:26][CH:27]=1.C([N:32](CC)CC)C>C(O)C.O1CCCC1.[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(OCC)(=O)C>[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]2[NH:32][C:10]([CH:9]([C:6]3[CH:5]=[CH:4][C:3]([S:2][CH3:1])=[CH:8][N:7]=3)[CH2:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:11][CH:12]=2)=[N:26][CH:27]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 101032675-Chloropyridine-2-carboxaldehydeHCID 593313384-[5-(methylsulfanyl)pyridin-2-yl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one

Product 1

HCID 68433023HCID 68433023, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 28333523-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chlorideCatalystHCID 8857Ethyl AcetateSolventHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution (3 mL) of 4-[5-(methylsulfanyl)pyridin-2-yl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one (89.0 mg) in ethanol-tetrahydrofuran (1:1) were added 5-chloropyridine-2-carbaldehyde (86.5 mg), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (8.2 mg) and triethylamine (17 μL), and the mixture was stirred with heating under reflux for 2 h After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was dried (MgSO4) and concentrated. To a solution of the obtained residue (MS: 433 (M)) in acetic acid (2 mL) was added ammonium acetate (376 mg), and the mixture was stirred at 110° C. for 1 hr. After cooling to room temperature, the mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution. The reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (117 mg, yield 92%) was obtained as a pale-yellow amorphous solid from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 2 h
  3. washwashed with water
  4. dry with materialThe ethyl acetate layer was dried (MgSO4)
  5. concentrationconcentrated
  6. additionTo a solution of the obtained residue (MS: 433 (M)) in acetic acid (2 mL) was added ammonium acetate (376 mg)
  7. stirringthe mixture was stirred at 110° C. for 1 hr
  8. temperatureAfter cooling to room temperature
  9. additionThe reaction mixture was diluted with ethyl acetate
  10. washwashed with water
  11. dry with materialThe ethyl acetate layer was dried (MgSO4)
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-3fe0ea99d5c14087b17c228e70476f49
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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