Trifluoroacetic acid → HCID 10023328, compound

HRID 1696916Notes

Reaction equation

HRID 1696916 reaction equation
[N:1]1([C:5]2[N:14]=[C:13]3[C:8]([C:9](=[O:29])[C:10]([C:26]([OH:28])=[O:27])=[CH:11][N:12]3CC3C=CC(OC)=CC=3OC)=[C:7]([CH3:30])[C:6]=2[F:31])[CH2:4][CH2:3][CH2:2]1.[F:32][C:33]([F:38])([F:37])[C:34]([OH:36])=[O:35]>>[F:31][C:6]1[C:7]([CH3:30])=[C:8]2[C:13](=[N:14][C:5]=1[NH:1][CH2:2][CH2:3][CH2:4][O:36][C:34](=[O:35])[C:33]([F:38])([F:37])[F:32])[NH:12][CH:11]=[C:10]([C:26]([OH:28])=[O:27])[C:9]2=[O:29]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67274950HCID 67274950, compound

Product 1

HCID 10023328HCID 10023328, compound

Procedure

A solution of Example 62A (0.55 mmol) in trifluoroacetic acid (15 mL) was heated to 80° C. for 16 hours and concentrated. The concentrate was dissolved in dichloromethane, washed with water, and filtered; and the filtrate was concentrated to provide the desired product and a small amount of 6-fluoro-5-methyl-4-oxo-7-(azetidin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid 7-azetidin-1-yl compound. NMR (300 MHz, DMSO-d6) δ 8.4 (s, 1H), 8.15 (m, 1H), 4.5 (m, 2H), 3.55 (m, 2H), 2.7 (m, 3H), 2.1 (m, 2H).

Workup

  1. concentrationconcentrated
  2. dissolutionThe concentrate was dissolved in dichloromethane
  3. washwashed with water
  4. filtrationfiltered
  5. concentrationand the filtrate was concentrated

Sources & evidence

ORD record
ord-7da8062452ce48148063153547705c8f
Source dataset
uspto-grants-2012_04
Patent number
US08163769B2

Reaction notes

Loading…