Triethylamine → N-[2-tert-butoxycarbamoyl-2-(4-methanesulphonylpiperazin-1-yl)ethyl]-4-but-2-ynyloxybenzamide

HRID 517492Notes

Reaction equation

HRID 517492 reaction equation
ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[CH2:23]([O:27][C:28]1[CH:51]=[CH:50][C:31]([C:32]([NH:34][CH2:35][CH:36]([N:40]2[CH2:45][CH2:44][N:43]([S:46]([CH3:49])(=[O:48])=[O:47])[CH2:42][CH2:41]2)[C:37](O)=[O:38])=[O:33])=[CH:30][CH:29]=1)[C:24]#[C:25][CH3:26].Cl.[C:53]([O:57][NH2:58])([CH3:56])([CH3:55])[CH3:54].C(N(CC)CC)C>ClCCl.CN(C)C=O>[C:53]([O:57][NH:58][C:37]([CH:36]([N:40]1[CH2:45][CH2:44][N:43]([S:46]([CH3:49])(=[O:48])=[O:47])[CH2:42][CH2:41]1)[CH2:35][NH:34][C:32](=[O:33])[C:31]1[CH:50]=[CH:51][C:28]([O:27][CH2:23][C:24]#[C:25][CH3:26])=[CH:29][CH:30]=1)=[O:38])([CH3:56])([CH3:55])[CH3:54]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 680883553-(4-But-2-ynyloxybenzoylamino)-2-(4-methanesulphonylpiperazin-1-yl)propanoic acid

Product 1

HCID 86667905N-[2-tert-butoxycarbamoyl-2-(4-methanesulphonylpiperazin-1-yl)ethyl]-4-but-2-ynyloxybenzamideYield 101.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

50 mg (0.4 mmol) of 1-hydroxybenzotriazole then 70 mg (0.4 mmol) of 1-ethyl-3-(3-dimethylamino-propyl)carbodiimide hydrochloride are added to a solution of 100 mg (0.2 mmol) of 3-(4-but-2-ynyloxybenzoylamino)-2-(4-methanesulphonylpiperazin-1-yl)propanoic acid in 2 ml of dichloromethane and 2 ml of dimethylformamide. The reaction medium is stirred for 20 min before adding a mixture containing 30 mg (0.3 mmol) of O-tert-butylhydroxylamine hydrochloride and 40 μl (0.3 mmol) of triethylamine. The mixture is then stirred at ambient temperature for 20 h. Dichloromethane is added, the organic phase is washed with a saturated aqueous solution of sodium hydrogen carbonate then with water, dried over magnesium sulphate, filtered and concentrated under vacuum. 100 mg (85%) of N-[2-tert-butoxycarbamoyl-2-(4-methanesulphonylpiperazin-1-yl)ethyl]-4-but-2-ynyloxy benzamide are obtained in the form of a white solid.

Workup

  1. additionbefore adding a mixture
  2. stirringThe mixture is then stirred at ambient temperature for 20 h
  3. washthe organic phase is washed with a saturated aqueous solution of sodium hydrogen carbonate
  4. dry with materialwith water, dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-27e8717dbe834a87addcc9b613fd60a4
Source dataset
uspto-grants-2015_08
Patent number
US09115102B2

Reaction notes

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