Sodium Bicarbonate → HCID 58691296, compound

HRID 602325Notes

Reaction equation

HRID 602325 reaction equation
Cl.CN(C)CCCN=C=NCC.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]([N:23]2[C@@H:27]([C:28]([OH:30])=O)[CH2:26][S:25][CH2:24]2)=[O:22])=[CH:16][CH:15]=1.[NH2:31][C:32]1[CH:37]=[CH:36][C:35]([N:38]2[CH2:43][CH2:42][O:41][CH2:40][C:39]2=[O:44])=[CH:34][CH:33]=1.C(=O)([O-])O.[Na+]>CN(C)C=O>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([NH:20][C:21]([N:23]2[C@@H:27]([C:28]([NH:31][C:32]3[CH:33]=[CH:34][C:35]([N:38]4[CH2:43][CH2:42][O:41][CH2:40][C:39]4=[O:44])=[CH:36][CH:37]=3)=[O:30])[CH2:26][S:25][CH2:24]2)=[O:22])=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 111948544-(4-Aminophenyl)morpholin-3-oneHCID 28374408HCID 28374408, compound

Product 1

HCID 58691296HCID 58691296, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.2 498 mg (2.60 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (DAPECI) are added to a solution of 573 mg (2.00 mmol) of (S)-3-(4-chlorophenylcarbamoyl)thiazolidine-4-carboxylic acid and 384 mg (2.00 mmol) of 4-(4-aminophenyl)morpholin-3-one in 4 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 3-N-[(4-chlorophenyl)]-4-N-{[4-(3-oxomorpholin-4-yl)phenyl]}-(S)-thiazolidine-3,4-dicarboxamide (“A3”) as a colourless solid; ESI 461.

Workup

  1. customthe precipitate formed
  2. filtrationis filtered off

Sources & evidence

ORD record
ord-8819ed3aaec94db8883144845e215d3b
Source dataset
uspto-grants-2011_03
Patent number
US07906516B2

Reaction notes

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