Ethyl 1-[2-(dimethylamino)ethyl]-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate → 1-[2-(Dimethylamino)ethyl]-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

HRID 1047118Notes

Reaction equation

HRID 1047118 reaction equation
[CH3:1][N:2]([CH3:42])[CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][C:11]([C:15]3[CH:16]=[N:17][C:18]([NH:30][C:31](=[O:35])[NH:32][CH2:33][CH3:34])=[CH:19][C:20]=3[C:21]3[S:22][CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[N:25]=3)=[CH:12][N:13]=2)[C:8](=[O:36])[C:7]([C:37]([O:39]CC)=[O:38])=[CH:6]1>C(O)C>[CH3:42][N:2]([CH3:1])[CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][C:11]([C:15]3[CH:16]=[N:17][C:18]([NH:30][C:31](=[O:35])[NH:32][CH2:33][CH3:34])=[CH:19][C:20]=3[C:21]3[S:22][CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[N:25]=3)=[CH:12][N:13]=2)[C:8](=[O:36])[C:7]([C:37]([OH:39])=[O:38])=[CH:6]1

Participants

3

Reactant 1

HCID 68748480Ethyl 1-[2-(dimethylamino)ethyl]-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Product 1

HCID 687483311-[2-(Dimethylamino)ethyl]-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acidYield 16.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred suspension of ethyl 1-[2-(dimethylamino)ethyl]-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (Example 15, 100 mg, 0.16 mmol) in ethanol (10 mL) 10% potassium hydroxide (0.3 mL) was added. The reaction mixture was heated to 90° C. for 1 h. After completion of the reaction, the reaction mixture was cooled to room temperature then concentrated under reduced pressure to a residue. The residue was diluted with water and acidified with 2N HCl to pH 2-3 to obtain a solid which was filtered, washed with water and dried to afford 50 mg of crude product. This was purified by preparative HPLC to give 15 mg (15%) of 1-[2-(dimethylamino)ethyl]-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid.

Workup

  1. additionwas added
  2. customAfter completion of the reaction
  3. temperaturethe reaction mixture was cooled to room temperature
  4. concentrationthen concentrated under reduced pressure to a residue
  5. additionThe residue was diluted with water
  6. customto obtain a solid which
  7. filtrationwas filtered
  8. washwashed with water
  9. customdried
  10. customto afford 50 mg of crude product
  11. customThis was purified by preparative HPLC

Sources & evidence

ORD record
ord-7b353c505d0b46929f0ead948b0305d8
Source dataset
uspto-grants-2013_10
Patent number
US08569484B2

Reaction notes

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