Acetohydrazide → HCID 67490884, compound

HRID 571963Notes

Reaction equation

HRID 571963 reaction equation
CO[C:3](OC)([N:5]([CH3:7])C)[CH3:4].[C:10]([NH:13][NH2:14])(=O)[CH3:11].N[C@H:16]1[CH2:21]C[CH2:19][C@@H:18]([NH:22][S:23]([C:26]2[C:31]([CH:32]([CH3:34])[CH3:33])=[CH:30][C:29]([CH:35]([CH3:37])[CH3:36])=[CH:28][C:27]=2[CH:38]([CH3:40])[CH3:39])(=[O:25])=[O:24])[CH2:17]1>C(#N)C>[CH3:11][C:10]1[N:5]([C@@H:7]2[CH2:21][CH2:16][CH2:17][C@H:18]([NH:22][S:23]([C:26]3[C:31]([CH:32]([CH3:34])[CH3:33])=[CH:30][C:29]([CH:35]([CH3:37])[CH3:36])=[CH:28][C:27]=3[CH:38]([CH3:39])[CH3:40])(=[O:25])=[O:24])[CH2:19]2)[C:3]([CH3:4])=[N:14][N:13]=1

Participants

5

Reactant 3

HCID 14039AcetohydrazideHCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 67491264HCID 67491264, compound

Product 1

HCID 67490884HCID 67490884, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of N,N-dimethylacetamide dimethylacetal (21.0 mg, 0.158 mmol) and acetic hydrazide (10.7 mg, 0.145 mmol) in acetonitrile (2.0 mL) was heated to 50° C. for 30 min, at which point, compound 7c (50.0 mg, 0.131 mmol) was added, and the resulting mixture was heated to 100° C. overnight. After cooling to rt, the reaction mixture was partitioned between EtOAc and water. The layers were separated, and the aq. layer was extracted with EtOAc. The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by preparative thin layer chromatography on silica gel (10% MeOH/DCM as eluent) to afford the title compound, 7d. m/z (ES) 461 (MH)+; IC50=9.8 nM

Workup

  1. additionwas added
  2. temperatureAfter cooling to rt
  3. customthe reaction mixture was partitioned between EtOAc and water
  4. customThe layers were separated
  5. extractionthe aq. layer was extracted with EtOAc
  6. washThe combined organics were washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude residue was purified by preparative thin layer chromatography on silica gel (10% MeOH/DCM as eluent)

Sources & evidence

ORD record
ord-ca97c216a018411eab8674bc88ea44fb
Source dataset
uspto-grants-2015_05
Patent number
US09029377B2

Reaction notes

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