Triethylamine → HCID 67513032, compound

HRID 244370Notes

Reaction equation

HRID 244370 reaction equation
Cl.[CH:2]([N:5]([C@@H:32]1[CH2:37][CH2:36][CH2:35][NH:34][CH2:33]1)[C:6]([C:8]1[C:9]([C:28]([F:31])([F:30])[F:29])=[CH:10][C:11]2[O:16][C:15]([CH3:18])([CH3:17])[C:14](=[O:19])[N:13]([CH2:20][CH2:21][NH:22][C:23](=[O:26])[CH2:24][CH3:25])[C:12]=2[CH:27]=1)=[O:7])([CH3:4])[CH3:3].C(N(CC)CC)C.Cl[C:46]([O:48][CH:49]([Cl:51])[CH3:50])=[O:47]>C(Cl)(Cl)Cl>[CH3:18][C:15]1([CH3:17])[C:14](=[O:19])[N:13]([CH2:20][CH2:21][NH:22][C:23](=[O:26])[CH2:24][CH3:25])[C:12]2[CH:27]=[C:8]([C:6]([N:5]([CH:2]([CH3:3])[CH3:4])[C@@H:32]3[CH2:37][CH2:36][CH2:35][N:34]([C:46]([O:48][CH:49]([Cl:51])[CH3:50])=[O:47])[CH2:33]3)=[O:7])[C:9]([C:28]([F:30])([F:29])[F:31])=[CH:10][C:11]=2[O:16]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5213051-Chloroethyl chloroformateHCID 67511771HCID 67511771, compound

Product 1

HCID 67513032HCID 67513032, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of N-isopropyl-2,2-dimethyl-3-oxo-N-[(3R)-piperidin-3-yl]-4-[2-(propionylamino)ethyl]-7-(trifluoromethyl)-3,4-dihydro-2H-1,4-benzoxazine-6-carboxamide hydrochloride (3.0 g) in chloroform (25 ml) were added successively triethylamine (0.98 ml) and 1-chloroethyl chloroformate (0.63 ml) under ice-cooling, and the mixture was stirred at room temperature overnight. After the reaction was completed, the reaction solution was washed with water and a saturated aqueous sodium chloride solution, dried over magnesium sulfate, and the solvent was concentrated to give the title compound (3.55 g) as white amorphous. The obtained title compound was used in the next reaction without further purification.

Workup

  1. temperaturecooling
  2. washthe reaction solution was washed with water
  3. dry with materiala saturated aqueous sodium chloride solution, dried over magnesium sulfate
  4. concentrationthe solvent was concentrated

Sources & evidence

ORD record
ord-7b97ea2bf04a4caa9d38307dd6d88965
Source dataset
uspto-grants-2014_02
Patent number
US08658639B2

Reaction notes

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