HCID 68749280, compound → HCID 68746318, compound

HRID 1047115Notes

Reaction equation

HRID 1047115 reaction equation
[CH2:1]([O:8][P:9]([O:19][CH2:20][CH2:21][N:22]1[C:31]2[C:26](=[CH:27][C:28]([C:32]3[CH:33]=[N:34][C:35]([NH:47][C:48](=[O:52])[NH:49][CH2:50][CH3:51])=[CH:36][C:37]=3[C:38]3[S:39][CH:40]=[C:41]([C:43]([F:46])([F:45])[F:44])[N:42]=3)=[CH:29][N:30]=2)[C:25](=[O:53])[C:24]([C:54]([O:56]CC)=[O:55])=[CH:23]1)([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.[OH-].[K+]>[CH2:12]([O:11][P:9]([O:19][CH2:20][CH2:21][N:22]1[C:31]2[C:26](=[CH:27][C:28]([C:32]3[CH:33]=[N:34][C:35]([NH:47][C:48](=[O:52])[NH:49][CH2:50][CH3:51])=[CH:36][C:37]=3[C:38]3[S:39][CH:40]=[C:41]([C:43]([F:46])([F:45])[F:44])[N:42]=3)=[CH:29][N:30]=2)[C:25](=[O:53])[C:24]([C:54]([OH:56])=[O:55])=[CH:23]1)([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 1

HCID 68749280HCID 68749280, compound

Product 1

HCID 68746318HCID 68746318, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14797Potassium HydroxideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred suspension of ethyl 1-(2-{[bis(benzyloxy)phosphoryl]oxy}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 30, 210 mg, 0.2511 mmol) in ethanol (20 mL), 10% potassium hydroxide (0.2 mL) was added. The reaction mixture was heated to 60° C. for 30 min. After completion of the reaction, the reaction mixture was cooled to room temperature and concentrated under reduced pressure to a residue. The residue was diluted with water and acidified with 2N hydrochloric acid solution to pH 4 to obtain solid which was filtered, washed with water and dried to afford 1-(2-{[bis(benzyloxy)phosphoryl]oxy}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 150 mg (84%).

Workup

  1. additionwas added
  2. customAfter completion of the reaction
  3. temperaturethe reaction mixture was cooled to room temperature
  4. concentrationconcentrated under reduced pressure to a residue
  5. additionThe residue was diluted with water
  6. customto obtain solid which
  7. filtrationwas filtered
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-520b8d577cd24423b33ad6786df0085b
Source dataset
uspto-grants-2013_10
Patent number
US08569484B2

Reaction notes

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