Triethylamine → HCID 15308004, compound

HRID 1289017Notes

Reaction equation

HRID 1289017 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 dropwise 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 NaHCO 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; Anal. Calc'd for C27 H22FN3O2S: C,68.8; H,4.7; N,8.9; F,4.0; S,6.8 Found: C,67.7; H,4.6; N,8.5; F,3.7; S,6.4.

Workup

  1. washThe reaction mixture is washed with H2O, saturated NaHCO 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-4febcc14e4554b43b174bfd302dbc78a
Source dataset
uspto-grants-1998_05
Patent number
US05747487

Reaction notes

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