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Sodium Hydroxide → 1-[2-Fluoro-4-(2-{[4-(4-methylpiperazin-1-yl)piperidine-1-carbonyl]amino}pyridin-4-yloxy)phenylcarbamoyl]cyclopropanecarboxylic acid

HRID 1712671
Notes
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Reaction equation

HRID 1712671 reaction equation
Cl.C([O:9][C:10]([C:12]1([C:15](=[O:47])[NH:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:29]=[CH:28][N:27]=[C:26]([NH:30][C:31]([N:33]4[CH2:38][CH2:37][CH:36]([N:39]5[CH2:44][CH2:43][N:42]([CH3:45])[CH2:41][CH2:40]5)[CH2:35][CH2:34]4)=[O:32])[CH:25]=3)=[CH:19][C:18]=2[F:46])[CH2:14][CH2:13]1)=[O:11])C1C=CC=CC=1.[OH-].[Na+]>O.C(OCC)(=O)C>[F:46][C:18]1[CH:19]=[C:20]([O:23][C:24]2[CH:29]=[CH:28][N:27]=[C:26]([NH:30][C:31]([N:33]3[CH2:38][CH2:37][CH:36]([N:39]4[CH2:40][CH2:41][N:42]([CH3:45])[CH2:43][CH2:44]4)[CH2:35][CH2:34]3)=[O:32])[CH:25]=2)[CH:21]=[CH:22][C:17]=1[NH:16][C:15]([C:12]1([C:10]([OH:11])=[O:9])[CH2:14][CH2:13]1)=[O:47]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 685015601-[2-Fluoro-4-(2-{[4-(4-methylpiperazin-1-yl)piperidine-1-carbonyl]amino}pyridin-4-yloxy)phenylcarbamoyl]cyclopropanecarboxylic acid benzyl ester hydrochloride

Product 1

HCID 247886301-[2-Fluoro-4-(2-{[4-(4-methylpiperazin-1-yl)piperidine-1-carbonyl]amino}pyridin-4-yloxy)phenylcarbamoyl]cyclopropanecarboxylic acidYield 74%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 8857Ethyl AcetateSolvent2×

Procedure

1-[2-Fluoro-4-(2-{[4-(4-methylpiperazin-1-yl)piperidine-1-carbonyl]amino}pyridin-4-yloxy)phenylcarbamoyl]cyclopropanecarboxylic acid benzyl ester hydrochloride (2 g) was dissolved in water (20 ml) and ethyl acetate (20 ml), and a 2N aqueous solution of sodium hydroxide (4 ml) was added, and the layers were separated. The organic layer was washed with water and concentrated. Addition of tetrahydrofuran and subsequent concentration was repeated three times. The residue was dissolved in a mixed solvent of tetrahydrofuran (8 ml) and water (1.6 ml), and palladium on carbon (200 mg) was added, and the mixture was stirred at room temperature under a hydrogen atmosphere (0.2 MPa) for 5 hours. Tetrahydrofuran (4 ml) and methanol (6 ml) were added to the reaction mixture, which was filtered. The residue was washed with 90% aqueous methanol (3 ml). Tetrahydrofuran (12 ml) and the seed crystals obtained in (Method 1) were added to the filtrate, and the mixture was stirred at room temperature for 1 hour. Ethyl acetate (32 ml) was added, and the mixture was stirred for 14 hours. The crystals were filtered and dried to give the title compound (1.2 g) as white crystals.

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with water
  3. concentrationconcentrated
  4. additionAddition of tetrahydrofuran and subsequent concentration
  5. dissolutionThe residue was dissolved in a mixed solvent of tetrahydrofuran (8 ml) and water (1.6 ml), and palladium on carbon (200 mg)
  6. additionwas added
  7. additionTetrahydrofuran (4 ml) and methanol (6 ml) were added to the reaction mixture, which
  8. filtrationwas filtered
  9. washThe residue was washed with 90% aqueous methanol (3 ml)
  10. customTetrahydrofuran (12 ml) and the seed crystals obtained in (Method 1)
  11. additionwere added to the filtrate
  12. stirringthe mixture was stirred at room temperature for 1 hour
  13. stirringthe mixture was stirred for 14 hours
  14. filtrationThe crystals were filtered
  15. customdried

Sources & evidence

ORD record
ord-145079498e6e400b87f7f91460d7ddcc
Source dataset
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07790885B2

Reaction notes

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