Hydrochloric Acid → HCID 68893702, compound

HRID 1786711Notes

Reaction equation

HRID 1786711 reaction equation
Cl.Cl.[NH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]([N:19]([CH:30]2[CH2:35][CH2:34][N:33]([CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH2:32][CH2:31]2)[C:20](=[O:29])[CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[CH3:18])[CH:12]=1.[Cl:43][CH2:44][C:45]([NH2:47])=[O:46].C(=O)([O-])[O-].[K+].[K+].Cl>C(#N)C.C(=O)(O)[O-].[Na+].C(OCC)(=O)C.CCOCC>[ClH:28].[ClH:43].[CH2:36]([N:33]1[CH2:34][CH2:35][CH:30]([N:19]([CH:17]([C:13]2[CH:12]=[C:11]([C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[CH2:4][NH:3][CH2:44][C:45]([NH2:47])=[O:46])[CH:16]=[CH:15][CH:14]=2)[CH3:18])[C:20](=[O:29])[CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[CH2:31][CH2:32]1)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 6580ChloroacetamideHCID 11430Potassium CarbonateHCID 68893785HCID 68893785, compound

Product 1

HCID 68893702HCID 68893702, compoundYield 77%

Reagents, catalysts & solvents 4

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of the compound obtained in Example 43 (100 mg) in acetonitrile (10 ml) was added 2-chloroacetic acid amide (22 mg) and potassium carbonate (66 mg), and the mixture was stirred at room temperature for 72 hours, and at 60° C. for 6 hours. The reaction mixture was diluted with saturated sodium bicarbonate (100 ml), and extracted with ethyl acetate (50 ml) twice. The extracted solutions were combined, washed with saturated brine, dried with magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography to give a colorless amorphous substance (60 mg, 62%). To a solution of this amorphous substance (60 mg) in ethyl acetate (10 ml) was added 1 M hydrochloric acid in ether (0.5 ml), and the mixture was concentrated under reduced pressure, and purified by reprecipitation from ethanol-diethyl ether to give the title compound (42 mg) as a white powder.

Workup

  1. waitat 60° C. for 6 hours
  2. extractionextracted with ethyl acetate (50 ml) twice
  3. washwashed with saturated brine
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography
  7. customto give a colorless amorphous substance (60 mg, 62%)
  8. concentrationthe mixture was concentrated under reduced pressure
  9. custompurified by reprecipitation from ethanol-diethyl ether

Sources & evidence

ORD record
ord-e29922bd31954e4c9a42c73495a770ab
Source dataset
uspto-grants-2009_03
Patent number
US07507753B2

Reaction notes

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