Triethylamine → HCID 178485438, compound

HRID 455953Notes

Reaction equation

HRID 455953 reaction equation
[CH:1]1([CH:7]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([C:18]4[CH:22]=[CH:21][O:20][N:19]=4)=[CH:14][CH:13]=3)[C:10](=[O:23])[C:9]([OH:24])=[C:8]2[C:25](=[O:35])[C:26]2[CH:31]=[CH:30][C:29]([C:32]([OH:34])=O)=[CH:28][CH:27]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.CN.O[N:40]1[C:44]2C=CC=CC=2N=N1.CN(C)C1C=C[NH+]=CC=1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>O.C(OCC)(=O)C.CN(C=O)C>[CH:1]1([CH:7]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([C:18]4[CH:22]=[CH:21][O:20][N:19]=4)=[CH:14][CH:13]=3)[C:10](=[O:23])[C:9]([OH:24])=[C:8]2[C:25](=[O:35])[C:26]2[CH:31]=[CH:30][C:29]([C:32](=[O:34])[NH:40][CH3:44])=[CH:28][CH:27]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

10

Reactant 6

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27350204-(Dimethylamino)pyridiniumHCID 6364545Methylamine hydrochlorideHCID 178524388HCID 178524388, compound

Product 1

HCID 178485438HCID 178485438, compoundYield 64%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 5-cyclohexyl-3-hydroxy-1-(4-isoxazol-3-ylphenyl)-4-(4-carboxybenzoyl)-1,5-dihydropyrrol-2-one (0.095 g, 0.2 mmol) and DMF (2 mL) was added, methylamine hydrochloride (0.020 g, 0.3 mmol), 1-hydroxybenztriazole (0.041 g, 0.3 mmol), 4-dimethylaminopyridinium (0.005 g, 0.04 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.058 g, 0.3 mmol) and triethylamine (0.042 mL, 0.3 mmol). The mixture was stirred at r.t. for 1 hr. Ethyl acetate and water were added, and the precipitate was collected by filtration to give 5-cyclohexyl-3-hydroxy-1-(4-isoxazol-3-ylphenyl)-4-(4-methylcarbamoylbenzoyl)-1,5-dihydropyrrol-2-one (0.062 g, 64%) as pale yellow crystals.

Workup

  1. additionwas added
  2. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-396e7125370141c69712c233bcd07363
Source dataset
uspto-grants-2013_07
Patent number
US08497263B2

Reaction notes

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