Triethylamine → HCID 14555496, compound

HRID 232052Notes

Reaction equation

HRID 232052 reaction equation
Cl[C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8][N:9]2[CH:12]2[CH2:14][CH2:13]2)=[CH:4][C:3]=1[F:19].[CH3:20][C:21]([O:24][C:25](=[O:43])[NH:26][CH:27]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:28](=[O:35])[NH:29][CH:30]1[CH2:34][CH2:33][NH:32][CH2:31]1)([CH3:23])[CH3:22].C(N(CC)CC)C>C(#N)C>[CH:12]1([N:9]2[C:10]3[C:5](=[CH:4][C:3]([F:19])=[C:2]([N:32]4[CH2:33][CH2:34][CH:30]([NH:29][C:28](=[O:35])[CH:27]([NH:26][C:25]([O:24][C:21]([CH3:22])([CH3:20])[CH3:23])=[O:43])[CH2:36][C:37]5[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=5)[CH2:31]4)[N:11]=3)[C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8]2)[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 110551427-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acidHCID 14555493HCID 14555493, compound

Product 1

HCID 14555496HCID 14555496, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 14.1 g (50 mmol) of 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, 18.3 g (55 mmol) of [R-(R*,S*)]-[1-phenylmethyl-2-oxo-2-[(3-pyrrolidinyl)amino]ethyl]carbamic acid 1,1-dimethylethyl ester, 15.2 g (0.15 mol) of triethylamine and 200 ml of acetonitrile was heated at reflux for four hours. The solvent was removed in vacuo and the residue was dissolved in methylene chloride and washed with 100 ml of cold 1.0M hydrochloric acid and then water. After drying (MgSO4) and filtering, the solvent was removed in vacuo to give 26.2 g of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for four hours
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue was dissolved in methylene chloride
  5. washwashed with 100 ml of cold 1.0M hydrochloric acid
  6. dry with materialAfter drying (MgSO4)
  7. filtrationfiltering
  8. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-00a545bbae4c49d59e7b1df21e6bcdb2
Source dataset
uspto-grants-1989_07
Patent number
US04851418

Reaction notes

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