Triethylamine → HCID 22099750, compound

HRID 1457672Notes

Reaction equation

HRID 1457672 reaction equation
[NH:1]1[C:10]2[C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[NH:7][CH2:6][CH2:5][C:4]=2[CH:3]=[N:2]1.C(N(CC)CC)C.[F:22][C:23]1[CH:24]=[CH:25][C:26]([CH3:41])=[C:27]([CH:40]=1)[C:28]([NH:30][C:31]1[N:36]=[CH:35][C:34]([C:37](Cl)=[O:38])=[CH:33][CH:32]=1)=[O:29]>ClCCl>[NH:1]1[C:10]2[C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:37]([C:34]3[CH:33]=[CH:32][C:31]([NH:30][C:28](=[O:29])[C:27]4[CH:40]=[C:23]([F:22])[CH:24]=[CH:25][C:26]=4[CH3:41])=[N:36][CH:35]=3)=[O:38])[CH2:6][CH2:5][C:4]=2[CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 155082506-(5-Fluoro-2-methylbenzoyl)aminopyridine-3-carbonyl chlorideHCID 135719546HCID 135719546, compound

Product 1

HCID 22099750HCID 22099750, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.20 mol of 1,4,5,6-tetrahydropyrazolo[4,3-d][1]benzazepine, 0.80 mol of triethylamine is added 0.42 mol of 6-[(5-fluoro-2-methylbenzoyl)amino]pyridine-3-carbonyl chloride in 15 ml of dichloromethane. The mixture is stirred under argon for 16 hours and diluted with dichloromethane (25 ml). The mixture is washed with H2 O), 1MNaHCO3, brine and dried (Na2SO4). The solvent is removed and the residue in methanol-tetrahydrofurane(1:1) stirred with 1NNaOH for 5 hours. The mixture is neutralized with acetic acid and the solvent removed. To the residue is added H2O and the mixture extracted with ethyl acetate. The extract is washed with H2O, 1NHCl, 1MNaHCO3 and dried (Na2SO4). The solvent 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. washThe mixture is washed with H2 O), 1MNaHCO3, brine
  2. dry with materialdried (Na2SO4)
  3. customThe solvent is removed
  4. stirringthe residue in methanol-tetrahydrofurane(1:1) stirred with 1NNaOH for 5 hours
  5. customthe solvent removed
  6. additionTo the residue is added H2O
  7. extractionthe mixture extracted with ethyl acetate
  8. washThe extract is washed with H2O
  9. dry with material1NHCl, 1MNaHCO3 and dried (Na2SO4)
  10. customThe solvent removed under vacuum
  11. customthe residue chromatographed on silica gel with ethyl acetate-hexane as solvent

Sources & evidence

ORD record
ord-15d19f2109074788bd80b44d2308bcf1
Source dataset
uspto-grants-1998_12
Patent number
US05849735

Reaction notes

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