Triethylamine → HCID 11153031, compound

HRID 722709Notes

Reaction equation

HRID 722709 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(N(CC)CC)C.[C:20]1([CH:26]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:27](Cl)=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)Cl>[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:27](=[O:28])[CH:26]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)#[N:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 746372,2-Diphenylacetyl chlorideHCID 7377432-Amino-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carbonitrile

Product 1

HCID 11153031HCID 11153031, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 2-Amino-3-cyano-4,7-dihydro-5H-thieno[2,3-c]pyran (400 mg; 2.22 mmol) and triethylamine (0.93 mL; 6.66 mmol) in dry methylene chloride (10 mL) under nitrogen at room temperature was added diphenylacetyl chloride (768 mg; 3.33 mmol). After 72 h, the mixture was diluted with methylene chloride and washed with 1N HCl. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was triturated with cold diethyl ether and filtered to give 310 mg (37%) of N-(3-Cyano-4,7-dihydro-5H-thieno[2,3-c]pyran-2-yl)-2,2-diphenyl-acetamide as a white solid. ES-HRMS m/e calcd for C22H18N2O2S (M+H+) 375.1162, found 375.1165.

Workup

  1. washwashed with 1N HCl
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was triturated with cold diethyl ether
  6. filtrationfiltered

Sources & evidence

ORD record
ord-223d82f13a734d739cd19157f56bc5b0
Source dataset
uspto-grants-2006_11
Patent number
US07138529B2

Reaction notes

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