Ammonium Hydroxide → 6-[(1E)-3-{4-[(4-fluorophenoxy)methyl]piperidin-1-yl}-3-oxoprop-1-en-1-yl]-2-oxo-1,2,3,4-tetrahydro-1,8-naphthyridine-3-carboxamide

HRID 2172032Notes

Reaction equation

HRID 2172032 reaction equation
[F:1][C:2]1[CH:34]=[CH:33][C:5]([O:6][CH2:7][CH:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:32])/[CH:15]=[CH:16]/[C:17]3[CH:18]=[C:19]4[C:24](=[N:25][CH:26]=3)[NH:23][C:22](=[O:27])[CH:21]([C:28](OC)=[O:29])[CH2:20]4)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[OH-].[NH4+:36]>N>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][CH:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:32])/[CH:15]=[CH:16]/[C:17]3[CH:18]=[C:19]4[C:24](=[N:25][CH:26]=3)[NH:23][C:22](=[O:27])[CH:21]([C:28]([NH2:36])=[O:29])[CH2:20]4)[CH2:10][CH2:9]2)=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 52950569HCID 52950569, compound

Product 1

HCID 529505706-[(1E)-3-{4-[(4-fluorophenoxy)methyl]piperidin-1-yl}-3-oxoprop-1-en-1-yl]-2-oxo-1,2,3,4-tetrahydro-1,8-naphthyridine-3-carboxamideYield 12%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

A solution of methyl 6-[(1E)-3-{4-[(4-fluorophenoxy)methyl]piperidin-1-yl}-3-oxoprop-1-en-1-yl]-2-oxo-1,2,3,4-tetrahydro-1,8-naphthyridine-3-carboxylate (13 mg, 0.028 mmol) in ammonium hydroxide (33% in water, 0.5 mL) and in ammonia (2M in ethanol, 0.5 mL) was stirred at 90° C. for 1 h30. The mixture was concentrated to dryness and the residue was purified on preparative TLC (eluent: dichloromethane/MeOH 90/10) to give 6-[(1E)-3-{4-[(4-fluorophenoxy)methyl]piperidin-1-yl}-3-oxoprop-1-en-1-yl]-2-oxo-1,2,3,4-tetrahydro-1,8-naphthyridine-3-carboxamide (1.6 mg, 12%) as a white solid.

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. customthe residue was purified on preparative TLC (eluent: dichloromethane/MeOH 90/10)

Sources & evidence

ORD record
ord-5f2636cab70649019780997e1be98c66
Source dataset
uspto-grants-2015_06
Patent number
US09051321B2

Reaction notes

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