Triethylamine → HCID 14997439, compound

HRID 1460466Notes

Reaction equation

HRID 1460466 reaction equation
[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]3[CH:15]([C:16](O)=[O:17])[S:14][CH2:13][C:12](=[O:19])[C:11]=3[CH:20]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.P(C#N)(=O)(OCC)OCC.[NH2:31][C:32]1[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=1.C(N(CC)CC)C>CN(C=O)C.O>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]3[CH:15]([C:16]([NH:31][C:32]4[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=4)=[O:17])[S:14][CH2:13][C:12](=[O:19])[C:11]=3[CH:20]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 100093-AminopyridineHCID 76257Diethyl cyanophosphonateHCID 10613471HCID 10613471, compound

Product 1

HCID 14997439HCID 14997439, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In DMF (10 ml) was dissolved 6-cyclohexyl-3,4-dihydro-1H-2-benzothiopyran-4-one-1-carboxylic acid (500 mg) followed by addition of diethyl phosphorocyanidate (85%, 365 mg). The mixture was stirred for 30 minutes under ice-cooling and, then, 3-aminopyridine (160 mg) and triethylamine (202 mg) were added thereto. The reaction mixture was further stirred for one hour under ice-cooling and poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and the solvent was distilled off to give 6-cyclohexyl-N-(3-pyridyl)-3,4-dihydro-1H-2-benzothiopyran-4-one-1-carboxamide (490 mg, yield 79%). Recrystallization from ethyl acetate-hexane gave colorless plates.

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture was further stirred for one hour under ice-
  3. temperaturecooling
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialdried (MgSO4)
  7. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-3716d589b1f44fb5af3f3dba968d6763
Source dataset
uspto-grants-1991_12
Patent number
US05071841

Reaction notes

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