Triethylamine → N-[5-[(6,11-Dihydro-5H-dibenz[b,e]azepin-5-yl)carbonyl]-2-pyridinyl][1,1'-biphenyl]-2-carboxamide

HRID 1457673Notes

Reaction equation

HRID 1457673 reaction equation
[CH:1]1[C:11]2[CH2:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[CH2:7][NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:23]1([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]([NH:31][C:32]1[N:37]=[CH:36][C:35]([C:38](Cl)=[O:39])=[CH:34][CH:33]=1)=[O:30]>ClCCl.O>[CH:1]1[C:11]2[CH2:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[CH2:7][N:6]([C:38]([C:35]3[CH:34]=[CH:33][C:32]([NH:31][C:29]([C:24]4[C:23]([C:41]5[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=5)=[CH:28][CH:27]=[CH:26][CH:25]=4)=[O:30])=[N:37][CH:36]=3)=[O:39])[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 679746,11-Dihydro-5H-dibenz[b,e]azepineHCID 220997926-[([1,1'-Biphenyl]-2-ylcarbonyl)amino]-3-pyridinecarbonyl chloride

Product 1

HCID 22100012N-[5-[(6,11-Dihydro-5H-dibenz[b,e]azepin-5-yl)carbonyl]-2-pyridinyl][1,1'-biphenyl]-2-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a chilled (0° C.) solution of 0.293 g of 6,11-dihydro-5H-dibenz[b,e]azepine and 625 μL triethylamine in 3.5 ml of dichloromethane is added a solution of 0.657 g of 6-[([1,1'-biphenyl]-2-ylcarbonyl)amino]-3-pyridinecarbonyl chloride in 1.5 ml of dichloromethane. The mixture is stirred under argon at room temperature for 16 hours and diluted with 40 ml of dichloromethane and 20 ml of water. The organic layer is separated and 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 concentrated to dryness under vacuum. The residual solid is chromatographed on silica gel with ethyl acetate-hexane(1:1) as solvent to give the product as a glass. Crystallization from ethyl acetate gives 0.395 g of white crystals, m.p. 134°-142° C.

Workup

  1. customThe organic layer is separated
  2. washwashed with 20 ml each of 1M NaHCO3, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationThe solution is filtered through a thin pad of hydrous magnesium silicate
  5. concentrationthe filtrate concentrated to dryness under vacuum
  6. customThe residual solid is chromatographed on silica gel with ethyl acetate-hexane(1:1) as solvent

Sources & evidence

ORD record
ord-cb628f9464fe4da2b3783ca7f26ba640
Source dataset
uspto-grants-1998_12
Patent number
US05849735

Reaction notes

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