Potassium Carbonate → HCID 21886024, compound

HRID 722718Notes

Reaction equation

HRID 722718 reaction equation
[NH2:1][C:2]1[S:10][C:5]2[CH2:6][O:7][CH2:8][CH2:9][C:4]=2[C:3]=1[C:11]#[N:12].C(=O)([O-])[O-].[K+].[K+].[C:19]1([CH:25]([CH2:29][CH3:30])[C:26](Cl)=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(OCC)C>[C:11]([C:3]1[C:4]2[CH2:9][CH2:8][O:7][CH2:6][C:5]=2[S:10][C:2]=1[NH:1][C:26](=[O:27])[CH:25]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:29][CH3:30])#[N:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 981732-Phenylbutyryl chlorideHCID 7377432-Amino-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carbonitrile

Product 1

HCID 21886024HCID 21886024, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred suspension of 2-Amino-3-cyano-4,7-dihydro-5H-thieno[2,3-c]pyran (361 mg; 2.0 mmol; prepared as described in Example 2, Step 1) and potassium carbonate (1.40 g; 10.1 mmol) in diethylether (6.0 mL) was added 2-phenylbutyryl chloride dropwise. The resulting mixture was stirred at room temperature for 24 h. The solvent was then removed in vacuo, the residue taken up into methylene chloride and washed with water. The organic layer was dried (sodium sulfate) filtered and concentrated in vacuo to give crude product which was triturated with diethyl ether to provide 428 mg (66%) of N-(3-Cyano-4,7-dihydro-5H-thieno[2,3-c]pyran-2-yl)-2-phenyl-butyramide as a beige colored solid. EI-HRMS m/e calcd for C18H18N2O2S (M+) 326.1809, found 326.1809.

Workup

  1. customThe solvent was then removed in vacuo
  2. washwashed with water
  3. dry with materialThe organic layer was dried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give crude product which
  7. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-ef1f2603911e4bc387d6d70d1eb54c6b
Source dataset
uspto-grants-2006_11
Patent number
US07138529B2

Reaction notes

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