Pyridine → HCID 86613807, compound

HRID 2378131Notes

Reaction equation

HRID 2378131 reaction equation
[CH:1]([O:4][C:5]([N:7]1[C:16]2[C:11](=[N:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C@H:10]([NH:19][CH2:20][C:21]2[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([C:31]([F:34])([F:33])[F:32])[CH:22]=2)[CH2:9][C@@H:8]1[CH3:35])=[O:6])([CH3:3])[CH3:2].N1C=CC=CC=1.[C:42](OC(=O)C)(=[O:44])[CH3:43]>ClCCl>[CH:1]([O:4][C:5]([N:7]1[C:16]2[C:11](=[N:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C@H:10]([N:19]([C:42](=[O:44])[CH3:43])[CH2:20][C:21]2[CH:26]=[C:25]([C:27]([F:28])([F:29])[F:30])[CH:24]=[C:23]([C:31]([F:34])([F:33])[F:32])[CH:22]=2)[CH2:9][C@@H:8]1[CH3:35])=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 86613809HCID 86613809, compound

Product 1

HCID 86613807HCID 86613807, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Cool to 0° C. a suspension of (+/−)-cis-4-(3,5-bis-trifluoromethyl-benzylamino)-6-methoxy-2-methyl-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid isopropyl ester (0.210 g, 0.415 mmol) and pyridine (0.203 mL, 2.52 mmol) in dichloromethane (3 mL) under nitrogen. Add acetic anhydride (0.117 mL, 1. 247 mmol) dropwise. After the addition is complete, remove the cooling bath and warm the reaction to room temperature with stirring for 12 h. Dilute the mixture with dichloromethane (25 mL) and wash with saturated aqueous sodium bicarbonate (25 mL). Dry the organic layer over sodium sulfate, filter, and remove the solvent under reduced pressure. Purify the residue using silica gel chromatography, eluting with hexanes/ethyl acetate (gradient eluent, 0-30% ethyl acetate in hexane), to afford the title compound (0.196 g, 88%). MS (ES+): 548 (M+H).

Workup

  1. additionAfter the addition
  2. customremove the cooling bath
  3. temperaturewarm
  4. customthe reaction to room temperature
  5. washwash with saturated aqueous sodium bicarbonate (25 mL)
  6. dry with materialDry the organic layer over sodium sulfate
  7. filtrationfilter
  8. customremove the solvent under reduced pressure
  9. customPurify the residue
  10. washeluting with hexanes/ethyl acetate (gradient eluent, 0-30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-16763c7b9be04cdfa7264f3e12801a5e
Source dataset
uspto-grants-2008_12
Patent number
US07470705B2

Reaction notes

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