Acetyl chloride → HCID 67351816, compound

HRID 1672761Notes

Reaction equation

HRID 1672761 reaction equation
[CH2:1]([NH:3][C:4]1[N:5]=[CH:6][C:7]2[C:16](=[O:17])[N:15]([C:18]3[CH:19]=[C:20]([CH:26]=[CH:27][CH:28]=3)[C:21](OCC)=[O:22])[CH2:14][CH:13]3[N:9]([CH2:10][CH2:11][CH2:12]3)[C:8]=2[N:29]=1)[CH3:2].[NH2:30][NH2:31].[C:32](Cl)(=[O:34])[CH3:33].C(N(CC)CC)C>C(O)C.C(OCC)(=O)C>[C:32]([NH:30][NH:31][C:21](=[O:22])[C:20]1[CH:26]=[CH:27][CH:28]=[C:18]([N:15]2[CH2:14][CH:13]3[N:9]([CH2:10][CH2:11][CH2:12]3)[C:8]3[N:29]=[C:4]([NH:3][CH2:1][CH3:2])[N:5]=[CH:6][C:7]=3[C:16]2=[O:17])[CH:19]=1)(=[O:34])[CH3:33]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 9321HydrazineHCID 67351988HCID 67351988, compound

Product 1

HCID 67351816HCID 67351816, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Compound 18 (169 mg, 0.427 mmol) obtained in Example 18 was dissolved in ethanol (2.1 mL), and the mixture was stirred overnight at 80° C. after adding hydrazine.monohydrate (0.207 mL, 4.27 mmol). The reaction mixture was then concentrated under reduced pressure, and vacuum dried. The resulting residue was dissolved in DMF (2 mL), and stirred overnight after adding acetyl chloride (0.0455 mL, 0640 mmol) and triethylamine (0.119 mL, 0.854 mmol). Then, the reaction mixture was diluted with ethyl acetate, and washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate. The residue obtained upon concentration under reduced pressure was then purified by silica gel column chromatography to give the title compound (Compound 19) (74.0 mg, 41% (2 steps)).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure, and vacuum
  2. customdried
  3. dissolutionThe resulting residue was dissolved in DMF (2 mL)
  4. stirringstirred overnight
  5. washwashed with water and saturated brine
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customThe residue obtained upon concentration under reduced pressure
  8. customwas then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ec9a278cacfc4f02ad4ebdfcdc4c9c1b
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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