Sodium Bicarbonate → N-[4-(3-oxomorpholin-4-yl)phenyl]-3-(5-chlorothiophene-2-carbonyl)oxazolidine-5-carboxamide

HRID 602328Notes

Reaction equation

HRID 602328 reaction equation
Cl.CN(C)CCCN=C=NCC.[Cl:13][C:14]1[S:18][C:17]([C:19]([N:21]2[CH2:25][CH:24]([C:26]([OH:28])=O)[O:23][CH2:22]2)=[O:20])=[CH:16][CH:15]=1.[NH2:29][C:30]1[CH:35]=[CH:34][C:33]([N:36]2[CH2:41][CH2:40][O:39][CH2:38][C:37]2=[O:42])=[CH:32][CH:31]=1.C(=O)([O-])O.[Na+]>CN(C)C=O>[O:42]=[C:37]1[CH2:38][O:39][CH2:40][CH2:41][N:36]1[C:33]1[CH:32]=[CH:31][C:30]([NH:29][C:26]([CH:24]2[O:23][CH2:22][N:21]([C:19]([C:17]3[S:18][C:14]([Cl:13])=[CH:15][CH:16]=3)=[O:20])[CH2:25]2)=[O:28])=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 111948544-(4-Aminophenyl)morpholin-3-oneHCID 586912493-(5-Chlorothiophene-2-carbonyl)oxazolidine-5-carboxylic acid

Product 1

HCID 11604507N-[4-(3-oxomorpholin-4-yl)phenyl]-3-(5-chlorothiophene-2-carbonyl)oxazolidine-5-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.2 479 mg (2.50 mmol) of N-(3-dimethylaminopropyl)-N′-ethyl-carbodiimide hydrochloride (DAPECI) are added to a solution of 500 mg (1.91 mmol) of 3-(5-chlorothiophene-2-carbonyl)oxazolidine-5-carboxylic acid and 367 mg (1.91 mmol) of 4-(4-aminophenyl)morpholin-3-one in 5 ml of dimethylformamide (DMF), and the mixture is stirred at room temperature for 18 hours. The reaction mixture is added to saturated sodium hydrogencarbonate solution, and the precipitate formed is filtered off, giving N-[4-(3-oxomorpholin-4-yl)phenyl]-3-(5-chlorothiophene-2-carbonyl)oxazolidine-5-carboxamide (“A5”) as a colourless solid; ESI 436.

Workup

  1. customthe precipitate formed
  2. filtrationis filtered off

Sources & evidence

ORD record
ord-3b7c1de6f8e74a89bc56bd77208a609d
Source dataset
uspto-grants-2011_03
Patent number
US07906516B2

Reaction notes

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