Triethylamine → HCID 58826664, compound

HRID 1012299Notes

Reaction equation

HRID 1012299 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:26]=[CH:25][C:24]([C:27]([OH:29])=O)=[CH:23][C:9]=3[N:10]3[C:16]=2[C:15]2[CH:17]=[CH:18][C:19]([O:21][CH3:22])=[CH:20][C:14]=2[O:13][CH2:12][CH2:11]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.NC1(C(NC2C=C[C:42]([O:45][C:46](=[O:49])[CH:47]=[CH2:48])=[CH:41]C=2)=O)CCC1.[OH2:50].O[N:52]1[C:56]2[CH:57]=[CH:58][CH:59]=[CH:60][C:55]=2N=N1.Cl.C(N=C=N[CH2:67][CH2:68][CH2:69]N(C)C)C.C([N:75]([CH2:78][CH3:79])CC)C>CN(C)C=O.O>[CH:1]1([C:7]2[C:8]3[CH:26]=[CH:25][C:24]([C:27]([NH:75][C:78]4([C:79]([NH:52][C:56]5[CH:55]=[CH:60][C:59](/[CH:48]=[CH:47]/[C:46]([O:45][CH2:42][CH3:41])=[O:49])=[CH:58][CH:57]=5)=[O:50])[CH2:69][CH2:68][CH2:67]4)=[O:29])=[CH:23][C:9]=3[N:10]3[C:16]=2[C:15]2[CH:17]=[CH:18][C:19]([O:21][CH3:22])=[CH:20][C:14]=2[O:13][CH2:12][CH2:11]3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 23152347HCID 23152347, compoundHCID 86761358HCID 86761358, compound

Product 1

HCID 58826664HCID 58826664, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 12-cyclohexyl-3-methoxy-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylic acid (100 mg, 0.26 mmol) and ethyl (E)-3-{(4-[(1-aminocyclobutanecarbonyl)amino]phenyl}acrylate hydrochloride (74 mg, 0.26 mmol) in N,N-dimethylformamide (2 ml) were added 1-hydroxybenzotriazole monohydrate (59 mg, 0.38 mmol), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (73 mg, 0.38 mmol) and triethylamine (78 μl, 0.56 mmol) under ice-cooling, and the mixture was stirred at room temperature for 18 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was successively washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel chromatography (hexane:ethyl acetate-2:1-1:2). Hexane:diethyl ether (1:1) solution was added to the obtained residue, and the precipitated solid was collected by filtration, and washed with hexane:diethyl ether (1:1) solution. The obtained solid was dried in vacuo to give ethyl (E)-3-[4-({1-[(12-cyclohexyl-3-methoxy-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carbonyl)amino]cyclobutanecarbonyl}amino)phenyl]acrylate (102 mg, yield 60%).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was successively washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customthe obtained residue was purified by silica gel chromatography (hexane:ethyl acetate-2:1-1:2)
  8. additionHexane:diethyl ether (1:1) solution was added to the obtained residue
  9. filtrationthe precipitated solid was collected by filtration
  10. washwashed with hexane:diethyl ether (1:1) solution
  11. customThe obtained solid was dried in vacuo

Sources & evidence

ORD record
ord-1c93d250f8384324813a5e00e1a8381d
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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