Triethylamine → HCID 13772746, compound

HRID 868081Notes

Reaction equation

HRID 868081 reaction equation
Cl[C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8][N:9]2[CH2:12][CH3:13])=[CH:4][C:3]=1[F:18].C(OC([NH:26][CH2:27][CH:28]1[CH2:31][CH2:30][NH:29]1)=O)(C)(C)C.C(N(CC)CC)C>C(#N)C>[NH2:26][CH2:27][CH:28]1[CH2:31][CH2:30][N:29]1[C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8][N:9]2[CH2:12][CH3:13])=[CH:4][C:3]=1[F:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 127908597-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acidHCID 14280902tert-Butyl [(azetidin-2-yl)methyl]carbamate

Product 1

HCID 13772746HCID 13772746, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 1.08 g (4.0 mmol) of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, 0.93 g (5.0 mmol) of 2-[(t-butoxycarbonylamino)methyl]azetidine, 1.01 g (10 mmol) of triethylamine and 50 ml of acetonitrile was stirred at reflux for two hours. The solvent was removed in vacuo and the residue was dissolved in 25 ml of trifluoroacetic acid. After stirring at room temperature for two hours, the solvent was removed in vacuo. The residue was suspended in water and the pH adjusted to 11 with 10% sodium hydroxide. The resulting solution was filtered through a fiber glass pad to clarify and the filtrate acidified to pH 7.2 with 1M hydrochloric acid. The resulting precipitate was removed by filtration, washed successively with water, ethanol, ether and dried in vacuo to give 0.66 g (52%) of the title compound, mp 198°-200° C.

Workup

  1. temperatureat reflux for two hours
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in 25 ml of trifluoroacetic acid
  4. stirringAfter stirring at room temperature for two hours
  5. customthe solvent was removed in vacuo
  6. filtrationThe resulting solution was filtered through a fiber glass pad
  7. customThe resulting precipitate was removed by filtration
  8. washwashed successively with water, ethanol, ether
  9. customdried in vacuo

Sources & evidence

ORD record
ord-dea76f94e5be476cb639d21aeaa87f10
Source dataset
uspto-grants-1988_10
Patent number
US04777175

Reaction notes

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