Triethylamine → 2-{3-[3-(1H-Benzotriazol-5-yl)-ureido]-2-oxo-7-phenyl-5-o-tolyl-azepan-1-yl}-N-tert-butyl-acetamide

HRID 429724Notes

Reaction equation

HRID 429724 reaction equation
[N:1]1[C:5]2=[CH:6][CH:7]=[C:8](C(O)=O)[CH2:9][C:4]2=[N:3][N:2]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:20])C=CC=CC=1.C([N:32]([CH2:35]C)CC)C.[C:37]([NH:41][C:42](=[O:66])[CH2:43][N:44]1[CH:50]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH2:49][CH:48]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=2[CH3:63])[CH2:47][CH:46]([NH2:64])[C:45]1=[O:65])([CH3:40])([CH3:39])[CH3:38]>O1CCCC1.C1C=CC=CC=1>[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH:32][C:35](=[O:20])[NH:64][CH:46]3[CH2:47][CH:48]([C:57]4[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=4[CH3:63])[CH2:49][CH:50]([C:51]4[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=4)[N:44]([CH2:43][C:42]([NH:41][C:37]([CH3:40])([CH3:38])[CH3:39])=[O:66])[C:45]3=[O:65])=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 15908914N-(t-Butyl)-2-oxo-3-amino-5-(2-methylphenyl)-7-phenyl-2,3,4,5,6,7-hexahydroazepin-1-yl ethanoic amideHCID 534427314H-Benzo[d][1,2,3]triazole-5-carboxylic acid

Product 1

HCID 1784241622-{3-[3-(1H-Benzotriazol-5-yl)-ureido]-2-oxo-7-phenyl-5-o-tolyl-azepan-1-yl}-N-tert-butyl-acetamide

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a 35 mL round-bottomed flank equipped with nitrogen inlet and condenser were added 40 mg (0.25 mmol) benzotriazole-5-carboxylic acid, 10 mL dry benzene, 10 mL dry tetrahydrofuran, 0.058 mL (0.27 mmol) diphenylphosphoryl azide, and 0.034 mL (0.27 mmol) triethylamine. The reaction was refluxed for 1.5 hour, cooled briefly, and 100 mg (0.25 mmol) N-(t-butyl)-2-oxo-3-amino-5-(2-methylphenyl)-7-phenyl-2,3,4,5,6,7-hexahydroazepin-1-yl ethanoic amide (the more polar isomer from the preceding example) was added and refluxing continued for 10 hours. The reaction was cooled and evaporated the resulting residue was chromatographed on silica gel with methanol/methylene chloride as eluent to afford the title compound as a white amorphous solid, 53 mg (37%).

Workup

  1. customTo a 35 mL round-bottomed flank equipped with nitrogen inlet and condenser
  2. temperatureThe reaction was refluxed for 1.5 hour
  3. temperaturecooled briefly
  4. temperaturerefluxing
  5. temperatureThe reaction was cooled
  6. customevaporated the resulting residue
  7. customwas chromatographed on silica gel with methanol/methylene chloride as eluent

Sources & evidence

ORD record
ord-df9717887386411981caebee88efaea1
Source dataset
uspto-grants-2001_11
Patent number
US06319915B1

Reaction notes

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