Diisopropylethylamine → HCID 86751128, compound

HRID 1939214Notes

Reaction equation

HRID 1939214 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.[N:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]2[S:27][CH:28]=[C:29]([C:31](Cl)=[O:32])[N:30]=2)[CH:21]=1>ClCCl.O>[N:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]2[S:27][CH:28]=[C:29]([C:31]([C:2]3[S:1][C:10]4[CH2:9][CH2:8][CH2:7][CH2:6][NH:5][C:4]=4[CH:3]=3)=[O:32])[N:30]=2)[CH:21]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 118049715,6,7,8-Tetrahydro-4H-thieno[3,2-B]azepineHCID 229945452-(Pyridin-3-yl)-1,3-thiazole-4-carbonyl chloride

Product 1

HCID 86751128HCID 86751128, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a cooled (0° C.) solution of 2 mmol of 5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepine, 6 mmol of N,N-diisopropylethylamine in 8 ml of dichloromethane added 2.2 mmol of 2-(3-pyridinyl)thiazole-4-carbonyl chloride. The mixture is stirred at room temperature for 16 hours and diluted with 50 ml of dichloromethane and 25 ml of water. The organic layer is separated, washed with H2O, 1N NaHCO3, brine and dried (Na2SO4). The solvent is removed under vacuum and the residue chromatographed on silica gel with ethyl acetate-hexane as solvent to give the product as a solid.

Workup

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

Sources & evidence

ORD record
ord-ffc8f08ac5d94c06858cb726f0be69ec
Source dataset
uspto-grants-1997_12
Patent number
US05696112

Reaction notes

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