Methyl Acetate → HCID 178432570, compound

HRID 1984035Notes

Reaction equation

HRID 1984035 reaction equation
[OH:1][NH:2][C:3](=[NH:28])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C@H:11]2[CH2:16][CH2:15][C@H:14]([C:17]([N:19]3[CH2:24][CH2:23][N:22]([CH:25]([CH3:27])[CH3:26])[CH2:21][CH2:20]3)=[O:18])[CH2:13][CH2:12]2)=[CH:6][CH:5]=1.[H-].[Na+].[C:31](OC)(=O)[CH3:32]>C1COCC1>[CH:25]([N:22]1[CH2:21][CH2:20][N:19]([C:17]([C@H:14]2[CH2:15][CH2:16][C@H:11]([O:10][C:7]3[CH:8]=[CH:9][C:4]([C:3]4[N:28]=[C:31]([CH3:32])[O:1][N:2]=4)=[CH:5][CH:6]=3)[CH2:12][CH2:13]2)=[O:18])[CH2:24][CH2:23]1)([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 6584Methyl Acetate2×HCID 24758Sodium hydride2×HCID 178456382HCID 178456382, compound

Product 1

HCID 178432570HCID 178432570, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 0.1 g (0.26 mmol) of trans-N-Hydroxy-4-[4-(4-isopropyl-piperazine-1-carbonyl)-cyclohexyloxy]-benzamidine and 0.24 g of molecular sieves 4A in 3 ml THF, 17 mg (0.39 mmol, 55% purity) of sodium hydride was added and the mixture was stirred at 60° C. for 45 min. After cooling down, 0.1 ml (1.45 mmol) of methyl acetate was dropwised to the mixture and the mixture was refluxed for 5 hr. After that, 56 mg (1.28 mmol, 55% purity) of sodium hydride and 1 ml (14.5 mmol) of methyl acetate were added to the mixture. The mixture was refluxed for 16 hr. The mixture was filtered and the filtrate was evaporated. The residue was purified by column chromatography on silica gel eluting with dichloromethane and methanol=from 98:2 to 19:1, after that, purified with cyclohexane and ethyl acetate=from 3:1 to 2:1. The combined product fractions were evaporated to dryness to yield 0.022 g (20% yields) of the titled compound. MS (m/e): 413.4 (MH+).

Workup

  1. additionwas added
  2. temperatureAfter cooling down
  3. temperaturethe mixture was refluxed for 5 hr
  4. temperatureThe mixture was refluxed for 16 hr
  5. filtrationThe mixture was filtered
  6. customthe filtrate was evaporated
  7. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane and methanol=from 98:2 to 19:1
  8. customafter that, purified with cyclohexane and ethyl acetate=from 3:1 to 2:1
  9. customThe combined product fractions were evaporated to dryness
  10. customto yield

Sources & evidence

ORD record
ord-ab12df940d504030ab4c720ca2d64c3a
Source dataset
uspto-grants-2009_06
Patent number
US07544683B2

Reaction notes

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