Triethylamine → HCID 21467156, compound

HRID 2255989Notes

Reaction equation

HRID 2255989 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.[F:18][C:19]1[CH:20]=[CH:21][C:22]([CH3:37])=[C:23]([CH:36]=1)[C:24]([NH:26][C:27]1[N:32]=[CH:31][C:30]([C:33](Cl)=[O:34])=[CH:29][CH:28]=1)=[O:25]>ClCCl.O>[S:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][N:5]([C:33]([C:30]3[CH:29]=[CH:28][C:27]([NH:26][C:24](=[O:25])[C:23]4[CH:36]=[C:19]([F:18])[CH:20]=[CH:21][C:22]=4[CH3:37])=[N:32][CH:31]=3)=[O:34])[C:4]=2[CH:3]=[CH:2]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 118049715,6,7,8-Tetrahydro-4H-thieno[3,2-B]azepineHCID 155082506-(5-Fluoro-2-methylbenzoyl)aminopyridine-3-carbonyl chloride

Product 1

HCID 21467156HCID 21467156, compoundYield 42.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 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 1.17 g of 6-[(5-fluoro-2-methylbenzoyl)amino]pyridine-3-carbonyl chloride and the mixture is stirred overnight at room temperature under argon. The mixture is diluted with 50 ml of dichloromethane and 20 ml of water and the organic layer separated. The organic layer is washed with 20 ml each of 1M NaHCO3, brine and dried (Na2SO4). The solution is filtered through a thin pad of hydrous magnesium silicate and the filtrate evaporated, concentrated to dryness under vacuum to give a glass. Crystallization from ethyl acetate-hexane gives 0.35 g of white crystals, m.p. 178°-180° C.

Workup

  1. temperatureTo a cooled
  2. customthe organic layer separated
  3. washThe organic layer is washed with 20 ml each of 1M NaHCO3, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationThe solution is filtered through a thin pad of hydrous magnesium silicate
  6. customthe filtrate evaporated
  7. concentrationconcentrated to dryness under vacuum
  8. customto give a glass
  9. customCrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-260fa8c8c28d466a8146cfd320fe9e03
Source dataset
uspto-grants-1997_08
Patent number
US05654297

Reaction notes

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