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Sodium Carbonate → HCID 9956681, compound

HRID 1870726
Notes
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Reaction equation

HRID 1870726 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([N:7]([CH2:10][CH3:11])[CH2:8][CH3:9])=[O:6].[NH2:12][C:13]1[C:18]([Cl:19])=[CH:17][C:16]([C:20]([NH:22][CH2:23][CH:24]2[O:29][CH2:28][CH2:27][NH:26][CH2:25]2)=[O:21])=[C:15]([O:30][CH3:31])[CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[ClH:1].[NH2:12][C:13]1[C:18]([Cl:19])=[CH:17][C:16]([C:20]([NH:22][CH2:23][CH:24]2[O:29][CH2:28][CH2:27][N:26]([CH2:2][CH2:3][CH2:4][C:5]([N:7]([CH2:10][CH3:11])[CH2:8][CH3:9])=[O:6])[CH2:25]2)=[O:21])=[C:15]([O:30][CH3:31])[CH:14]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24348694-Chloro-N,N-diethyl-butyramideHCID 10859540Benzamide, 4-amino-5-chloro-2-methoxy-N-(2-morpholinylmethyl)-

Product 1

HCID 9956681HCID 9956681, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4-chloro-N,N-diethylbutanamide (2.16 g), 4-amino-5-chloro-2-methoxy-N-(2-morpholinylmethyl)benzenamide (3 g), prepared following the procedure as described in EP-A-0,243,959, and sodium carbonate (1.58 g) in N,N-dimethyl-formamide (90 ml) was stirred for 48 hours at 70° C. The solvent was evaporated and water was added to the residue. This mixture was extracted twice with dichloromethane and the combined extracts were washed with water, dried, filtered and the solvent evaporated. The residue was purified by column chromatography over silica gel (eluent: CHCl3 /CH3OH 95/5). The first fraction was collected and the solvent was evaporated. The residue was converted into the hydrochloric salt in 2-propanol and diisopropyl ether. The salt was filtered off and crystallized from acetonitrile. The precipitate was filtered off and dried, yielding 1.43 g (30.4%) of (±)-2-[[(4-amino-5-chloro-2-methoxybenzoyl)amino]methyl]-N,N-diethyl4-morpholine-butanamide monohydrochloride. hemihydrate (compound 1; mp. 122.2° C.).

Workup

  1. customprepared
  2. customThe solvent was evaporated
  3. additionwater was added to the residue
  4. extractionThis mixture was extracted twice with dichloromethane
  5. washthe combined extracts were washed with water
  6. customdried
  7. filtrationfiltered
  8. customthe solvent evaporated
  9. customThe residue was purified by column chromatography over silica gel (eluent: CHCl3 /CH3OH 95/5)
  10. customThe first fraction was collected
  11. customthe solvent was evaporated
  12. filtrationThe salt was filtered off
  13. customcrystallized from acetonitrile
  14. filtrationThe precipitate was filtered off
  15. customdried

Sources & evidence

ORD record
ord-a481bb4934114699a802bf96463a0684
Source dataset
uspto-grants-2000_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06100262

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes