Hydrochloric Acid → HCID 22322436, compound

HRID 1059018Notes

Reaction equation

HRID 1059018 reaction equation
Cl.[Cl:2][C:3]1[CH:28]=[CH:27][C:6]([C:7]([CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][NH:17][C:18](=[O:26])[C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([OH:25])[CH:20]=3)[CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1.Cl[CH2:30][C:31]([NH:33][CH3:34])=[O:32].O.Cl>CN(C=O)C.C(OCC)(=O)C>[ClH:2].[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([CH:9]2[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][NH:17][C:18](=[O:26])[C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:30][C:31]([NH:33][CH3:34])=[O:32])[CH:20]=3)[CH2:13][CH2:14]2)=[O:8])=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 667732-chloro-N-methylacetamideHCID 22322240HCID 22322240, compound

Product 1

HCID 22322436HCID 22322436, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

The product of step (iii) above (0.10 g) was dissolved in DMF (3 ml), Cs2CO2 (0.23 g) and 2-chloro-N-methylacetamide (0.26 g) were added and the mixture heated at 80° C. for 16 hours. The mixture was cooled to room temperature, water and ethyl acetate were added and the organic phase separated. Evaporation of the solvent gave a gum which was treated with 1.0M ethereal hydrogen chloride solution to give the titled product as a solid (0.05 g).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customthe organic phase separated
  3. customEvaporation of the solvent
  4. customgave a gum which

Sources & evidence

ORD record
ord-9791bd2c451e43ffa507749f31ce7573
Source dataset
uspto-grants-2003_02
Patent number
US06518286B1

Reaction notes

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