Triethylamine → HCID 21467140, compound

HRID 1939219Notes

Reaction equation

HRID 1939219 reaction equation
[S:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][NH:5][C:4]=2[CH:3]=[CH:2]1.C(N(CC)CC)C.[CH3:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][C:26]([NH:28][C:29]1[N:34]=[CH:33][C:32]([C:35](Cl)=[O:36])=[CH:31][CH:30]=1)=[O:27]>ClCCl>[S:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][N:5]([C:35]([C:32]3[CH:31]=[CH:30][C:29]([NH:28][C:26](=[O:27])[CH2:25][C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[CH3:18])=[N:34][CH:33]=3)=[O:36])[C:4]=2[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 118049715,6,7,8-Tetrahydro-4H-thieno[3,2-B]azepineHCID 22099893HCID 22099893, compound

Product 1

HCID 21467140HCID 21467140, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cooled (0° C.) mixture of 0.306 g of 5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepine and 1.11 μl of triethylamine in 5 ml of dichloromethane is added 1.2 g of 6-[(2-methylphenylacetyl)amino]pyridine-3-carbonyl chloride. The mixture is stirred at room temperature for 16 hours and diluted with 50 ml of dichloromethane. The mixture is washed with H2O, 1N NaHCO3, H2O, brine and dried (Na2SO4). The solution is concentrated to dryness under vacuum and the residue chromatographed on silica gel to give the product as a solid.

Workup

  1. temperatureTo a cooled
  2. washThe mixture is washed with H2O, 1N NaHCO3, H2O, brine
  3. dry with materialdried (Na2SO4)
  4. concentrationThe solution is concentrated to dryness under vacuum
  5. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-7441b58fb0bb487690e405980d1f5337
Source dataset
uspto-grants-1997_12
Patent number
US05696112

Reaction notes

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