HCID 12148681, compound → HCID 178461605, compound

HRID 1243808Notes

Reaction equation

HRID 1243808 reaction equation
[NH2:1][C@:2]([C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1)([C:15]1[CH:20]=[CH:19][N:18]=[C:17]([F:21])[CH:16]=1)[C@@H:3]([NH:5][C:6]([C:8]1[NH:9][C:10](=[O:14])[CH:11]=[CH:12][CH:13]=1)=O)[CH3:4]>C1(C)C=CC=CC=1>[F:28][C:25]1[CH:26]=[CH:27][C:22]([C@@:2]2([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([F:21])[CH:16]=3)[C@H:3]([CH3:4])[NH:5][C:6]([C:8]3[NH:9][C:10](=[O:14])[CH:11]=[CH:12][CH:13]=3)=[N:1]2)=[CH:23][CH:24]=1

Participants

3

Reactant 1

HCID 12148681HCID 12148681, compound

Product 1

HCID 178461605HCID 178461605, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-[(1S,2R)-2-amino-2-(4-fluorophenyl)-2-(2-fluoro-4-pyridyl)-1-methylethyl]-6-oxo-1,6-dihydro-2-pyridine-carboxamide (16 g) was suspended in toluene (400 mL), and the suspension was heated under reflux for 10 hours while removing water azeotropically. The reaction mixture was concentrated in vacuo and the residue was purified by column chromatography (ethyl acetate:methanol=100:0→10:1) to give the title compound as a yellow oil. The yellow oil was dissolved in isopropanol (80 mL), and to this solution was added water (130 mL) at room temperature. The solution was allowed to stand at room temperature for 3 hours to give a colorless crystal, which was then collected by filtration. The crystal was suspended in water (500 mL) and the suspension was stirred at room temperature for 14 hours. The resulting crystal was collected again by filtration and dried in vacuo at 30° C. for 24 hours to give the title compound (crystal form A)(11.2 g) as a colorless massive crystal (m.p. 125–126° C.).

Workup

  1. temperaturethe suspension was heated
  2. temperatureunder reflux for 10 hours
  3. customwhile removing water azeotropically
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. customthe residue was purified by column chromatography (ethyl acetate:methanol=100:0→10:1)

Sources & evidence

ORD record
ord-edec3209d59145db902d53ce146df1b0
Source dataset
uspto-grants-2006_10
Patent number
US07119107B2

Reaction notes

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