Diisopropylethylamine → HCID 21467168, compound

HRID 2255986Notes

Reaction equation

HRID 2255986 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)C(C)C)(C)C.C[C:21]1[CH:25]=[CH:24][O:23][C:22]=1[CH2:26][C:27]([NH:29][C:30]1[N:35]=[CH:34][C:33]([C:36](Cl)=[O:37])=[CH:32][CH:31]=1)=[O:28]>C(Cl)Cl.O>[S:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][N:5]([C:36]([C:33]3[CH:32]=[CH:31][C:30]([NH:29][C:27]([C:26]4[CH:25]=[CH:24][O:23][C:22]=4[CH3:21])=[O:28])=[N:35][CH:34]=3)=[O:37])[C:4]=2[CH:3]=[CH:2]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 118049715,6,7,8-Tetrahydro-4H-thieno[3,2-B]azepineHCID 22099951HCID 22099951, compound

Product 1

HCID 21467168HCID 21467168, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2 mmol of 5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepine, 5 mmol of N,N-diisopropylethylamine and 2.2 mmol of 6-[(3-methyl-2-furanylacetyl)amino]pyridine-3-carbonyl chloride in 10 ml of CH2Cl2 is stirred at room temperature for 16 hours. The mixture is diluted with 50 ml of CH2Cl2 and 25 ml of water and the organic layer separated. The organic layer is washed with H2O, 1N NaHCO3, brine and dried (Na2SO4). The solvent is removed and the residue is chromatographed on silica gel with ethyl acetate-hexane as solvent to give the product as a solid.

Workup

  1. customthe organic layer separated
  2. washThe organic layer is washed with H2O, 1N NaHCO3, brine
  3. dry with materialdried (Na2SO4)
  4. customThe solvent is removed
  5. customthe residue is chromatographed on silica gel with ethyl acetate-hexane as solvent

Sources & evidence

ORD record
ord-5744045005d04855aea12710b13b65b0
Source dataset
uspto-grants-1997_08
Patent number
US05654297

Reaction notes

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