Acetic Anhydride → HCID 86613803, compound

HRID 2378126Notes

Reaction equation

HRID 2378126 reaction equation
[CH:1]([O:4][C:5]([N:7]1[C:16]2[C:11](=[N:12][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:14][CH:15]=2)[C@H:10]([N:21]([CH2:26][C:27]2[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[C:29]([C:37]([F:40])([F:39])[F:38])[CH:28]=2)[C:22]([NH2:25])=[N:23][OH:24])[CH2:9][C@@H:8]1[CH2:41][CH3:42])=[O:6])([CH3:3])[CH3:2].[C:43](OC(=O)C)(=O)[CH3:44]>>[CH:1]([O:4][C:5]([N:7]1[C:16]2[C:11](=[N:12][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:14][CH:15]=2)[C@H:10]([N:21]([CH2:26][C:27]2[CH:28]=[C:29]([C:37]([F:40])([F:39])[F:38])[CH:30]=[C:31]([C:33]([F:34])([F:35])[F:36])[CH:32]=2)[C:22]2[N:25]=[C:43]([CH3:44])[O:24][N:23]=2)[CH2:9][C@@H:8]1[CH2:41][CH3:42])=[O:6])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 86613804HCID 86613804, compound

Product 1

HCID 86613803HCID 86613803, compound

Conditions

Temperature
80 °C

Procedure

To (+/−)-cis-4-[N-(3,5-bis-trifluoromethyl-benzyl)-hydroxyguanidino]-2-ethyl-6-trifluoromethyl-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid isopropyl ester (80 mg, 0.13 mmol), add acetic anhydride (0.5 mL). Seal the tube and heat the reaction mixture at 80° C. overnight. Cool down the mixture and remove the solvents under reduced pressure. Add 2 N NaOH (2 mL) and ether to the crude material. Separate the layers, and extract the aqueous phase with ether. Dry the combined organic phase, filter, and concentrate in vacuo. Purify the residue by flash chromatography, eluting with hexanes/ethyl acetate, to afford the title compound (32 mg, %). MS (ES+): 640 (M+H).

Workup

  1. customSeal the tube
  2. temperatureCool down the mixture
  3. customremove the solvents under reduced pressure
  4. additionAdd 2 N NaOH (2 mL) and ether to the crude material
  5. customSeparate the layers
  6. extractionextract the aqueous phase with ether
  7. customDry the combined organic phase
  8. filtrationfilter
  9. concentrationconcentrate in vacuo
  10. customPurify the residue by flash chromatography
  11. washeluting with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-d46bbe86ae0342e2a7013f5118161f0c
Source dataset
uspto-grants-2008_12
Patent number
US07470705B2

Reaction notes

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