Triethylamine → HCID 15308004, compound

HRID 362438Notes

Reaction equation

HRID 362438 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH2:5][CH2:6][N:7]([C:16](=[O:24])[C:17]3[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=3)[C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[C:10]=2[N:11]=1.C(N(CC)CC)C.[CH3:32][C:33]1[CH:41]=[CH:40][C:39]([F:42])=[CH:38][C:34]=1[C:35](Cl)=[O:36]>C(Cl)Cl>[CH3:1][C:2]1[S:3][C:4]2[CH2:5][CH2:6][N:7]([C:16]([C:17]3[CH:18]=[CH:19][C:20]([NH:23][C:35](=[O:36])[C:34]4[CH:38]=[C:39]([F:42])[CH:40]=[CH:41][C:33]=4[CH3:32])=[CH:21][CH:22]=3)=[O:24])[C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[C:10]=2[N:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27373835-Fluoro-2-methylbenzoyl chlorideHCID 53876093HCID 53876093, compound

Product 1

HCID 15308004HCID 15308004, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 0.235 g of 5,6-dihydro-2-methyl-6-(4-aminobenzoyl)4H-thiazolo[5,4-d][1]benzazepine in 6 ml of methylene chloride under argon is added 107 μl of triethylamine followed by the drop-wise addition of 2-methyl-5-fluorobenzoyl chloride in 1 ml of methylene chloride. Stirring is continued at room temperature for 18 hours. The reaction mixture is washed with H2O, saturated NaHCO3 and brine. The organic layer is treated with activated carbon, filtered through MgSO4 and the filtrate evaporated in vacuo to a residue which is chromatographed on silica gel by elution with 15% ethyl acetate in methylene chloride to give 300 mg of the desired product as a white solid;

Workup

  1. washThe reaction mixture is washed with H2O, saturated NaHCO3 and brine
  2. additionThe organic layer is treated with activated carbon
  3. filtrationfiltered through MgSO4
  4. customthe filtrate evaporated in vacuo to a residue which
  5. customis chromatographed on silica gel by elution with 15% ethyl acetate in methylene chloride

Sources & evidence

ORD record
ord-6fe46049f83044288b35373fa05a508f
Source dataset
uspto-grants-1999_02
Patent number
US05869483

Reaction notes

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