Triethylamine → HCID 59853906, compound

HRID 2374846Notes

Reaction equation

HRID 2374846 reaction equation
[CH:1]1([O:7][C:8]([NH:10][CH2:11][C:12]([OH:14])=O)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:15]1[C:25]2[CH:24]=[CH:23][C:22]3[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=3[C:20](=[C:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)[C:19]=2[CH:18]=[CH:17][CH:16]=1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>ClCCl>[CH:15]1[C:25]2[CH:24]=[CH:23][C:22]3[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=3[C:20](=[C:30]3[CH2:31][CH2:32][N:33]([C:12](=[O:14])[CH2:11][NH:10][C:8](=[O:9])[O:7][CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]4)[CH2:34][CH2:35]3)[C:19]=2[CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 1597184-(5H-Dibenzo(a,d)cyclohepten-5-ylidene)piperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 13240890HCID 13240890, compound

Product 1

HCID 59853906HCID 59853906, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

86.1 mg (0.428 mmol) of {[(cyclohexyloxy)carbonyl]amino}acetic acid, 176 mg (0.642 mmol) of 4-(5H-dibenzo[a,d][7]annulen-5-ylidene)piperidine and 98.5 mg (0.514 mmol) of 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride were suspended in 10 ml of dichloromethane. 0.086 ml (0.617 mmol) of triethylamine was added to the obtained suspension, and they were stirred at room temperature for 3 hours. The resultant mixture was concentrated under reduced pressure and then ethyl acetate was added to the residue. The resultant mixture was washed with saturated aqueous sodium hydrogencarbonate solution, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The obtained residue was purified by the silica gel chromatography (hexane:ethyl acetate=95:5 to 1:4) to obtain the title compound.

Workup

  1. concentrationThe resultant mixture was concentrated under reduced pressure
  2. additionethyl acetate was added to the residue
  3. washThe resultant mixture was washed with saturated aqueous sodium hydrogencarbonate solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by the silica gel chromatography (hexane:ethyl acetate=95:5 to 1:4)

Sources & evidence

ORD record
ord-f5305f45ecae4d7983916d3218d59579
Source dataset
uspto-grants-2008_12
Patent number
US07462630B2

Reaction notes

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