Hydrochloric Acid → HCID 71735900, compound

HRID 715144Notes

Reaction equation

HRID 715144 reaction equation
Cl.[CH3:2][C:3]([CH3:33])([CH3:32])[CH2:4][CH2:5][NH:6][C:7](=[O:31])[NH:8][C:9]1[CH:10]=[C:11]([C:16]2[C:17]([CH3:30])=[N:18][C:19]3[C:24]([CH:25]=2)=[CH:23][N:22]=[C:21]([NH:26]C(=O)C)[CH:20]=3)[CH:12]=[CH:13][C:14]=1[F:15]>CCO>[NH2:26][C:21]1[CH:20]=[C:19]2[C:24]([CH:25]=[C:16]([C:11]3[CH:12]=[CH:13][C:14]([F:15])=[C:9]([NH:8][C:7]([NH:6][CH2:5][CH2:4][C:3]([CH3:32])([CH3:2])[CH3:33])=[O:31])[CH:10]=3)[C:17]([CH3:30])=[N:18]2)=[CH:23][N:22]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71735419HCID 71735419, compound

Product 1

HCID 71735900HCID 71735900, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add HCl (3M, 4 mL, 12 mmol) to a suspension of N-(3-(3-(3-(3,3-dimethylbutyl)ureido)-4-fluorophenyl)-2-methyl-1,6-naphthyridin-7-yl)acetamide (70 mg, 0.160 mmol) in EtOH (4 mL), stir at RT for 1.5 h, then heat at 50° C. for 4 h. Cool to RT, remove the organics under reduced pressure and filter the aqueous residue. Add satd. NaHCO3 to the filtrate until pH=8, extract with THF (3×), wash the combined organics with brine, dry over MgSO4 and concentrate to dryness. Suspend the material in 4:1 MeCN/H2O, collect the solid via filtration and dry to afford the title compound (47 mg, 74%) as a golden-tan solid. MS (ESI) m/z: 396.2 (M+H+).

Workup

  1. temperatureheat at 50° C. for 4 h
  2. temperatureCool to RT
  3. customremove the organics under reduced pressure
  4. filtrationfilter the aqueous residue
  5. additionAdd satd
  6. extractionNaHCO3 to the filtrate until pH=8, extract with THF (3×)
  7. washwash the combined organics with brine
  8. dry with materialdry over MgSO4
  9. concentrationconcentrate to dryness
  10. customcollect the solid
  11. filtrationvia filtration
  12. customdry

Sources & evidence

ORD record
ord-9b69d2ac515043ca879794ebe83a943a
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

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