7-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid → HCID 71565879, compound

HRID 1525121Notes

Reaction equation

HRID 1525121 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].[NH:20]1[CH2:23][CH:22]([NH:24][CH2:25][C@H:26]2[O:30][C:29](=[O:31])[N:28]([C:32]3[CH:33]=[CH:34][C:35]4[S:40][CH2:39][C:38](=[O:41])[NH:37][C:36]=4[CH:42]=3)[CH2:27]2)[CH2:21]1>CC#N.O>[CH:12]1([N:9]2[C:10]3[C:5](=[CH:4][C:3]([F:19])=[C:2]([N:20]4[CH2:23][CH:22]([NH:24][CH2:25][C@H:26]5[O:30][C:29](=[O:31])[N:28]([C:32]6[CH:33]=[CH:34][C:35]7[S:40][CH2:39][C:38](=[O:41])[NH:37][C:36]=7[CH:42]=6)[CH2:27]5)[CH2:21]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 2

HCID 110551427-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acidHCID 66954534HCID 66954534, compound

Product 1

HCID 71565879HCID 71565879, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid (commercial; 141 mg), 6-[(5R)-5-[(3-azetidinylamino)methyl]-2-oxo-3-oxazolidinyl]-2H-1,4-benzothiazin-3(4H)-one (prepared according to WO 2008/126034; 167 mg) and TEA (0.15 ml) in MeCN (4 ml) was heated at 75° C. for 2 h. The reaction mixture was allowed to reach rt, diluted with water, filtered and the solid was washed with MeOH and EA, affording a beige solid.

Workup

  1. customto reach rt
  2. filtrationfiltered
  3. washthe solid was washed with MeOH and EA
  4. customaffording a beige solid

Sources & evidence

ORD record
ord-ac4a5dc2dd8b48d9a53dc5e8e44a05a3
Source dataset
uspto-grants-2015_07
Patent number
US09079922B2

Reaction notes

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