Triethylamine → HCID 25206945, compound

HRID 600727Notes

Reaction equation

HRID 600727 reaction equation
Cl[C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:23])[C:7]([C:20]([OH:22])=[O:21])=[CH:8][N:9]2[C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[F:19])=[CH:4][C:3]=1[F:24].FC(F)(F)C([O-])=O.FC(F)(F)C(O)=O.[Cl:39][C:40]1[CH:45]=[CH:44][C:43]([C:46]2[C@@H:50]3[CH2:51][NH:52][CH2:53][C@@H:49]3[O:48][N:47]=2)=[CH:42][CH:41]=1.C(N(CC)CC)C>C(#N)C>[Cl:39][C:40]1[CH:41]=[CH:42][C:43]([C:46]2[CH:50]3[CH2:51][N:52]([C:2]4[N:11]=[C:10]5[C:5]([C:6](=[O:23])[C:7]([C:20]([OH:22])=[O:21])=[CH:8][N:9]5[C:12]5[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=5[F:19])=[CH:4][C:3]=4[F:24])[CH2:53][CH:49]3[O:48][N:47]=2)=[CH:44][CH:45]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 84468TrifluoroacetateHCID 105460847-Chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acidHCID 68972175HCID 68972175, compound

Product 1

HCID 25206945HCID 25206945, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

7-Chloro-1-(2,4-difluorophenyl-6-fluoro-4-oxo-1,4-dihydronapthyridine-3-carboxylic acid (50) (120 mg; 0.34 mmol), trifluoroacetate salt 4a (131 mg; 0.39 mmol) and triethylamine (0.3 mL) in acetonitrile (3 mL) were heated at reflux temperature overnight. After cooling, the volatiles were evaporated. The residue was triturated with water, filtered and dried to yield acid 101 as an off-white solid.

Workup

  1. temperatureat reflux temperature overnight
  2. temperatureAfter cooling
  3. customthe volatiles were evaporated
  4. customThe residue was triturated with water
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-7a2b301fdb0649168cfd7eadff10c1ec
Source dataset
uspto-grants-2011_03
Patent number
US07902227B2

Reaction notes

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