HCID 86724284, compound → HCID 72202470, compound

HRID 594912Notes

Reaction equation

HRID 594912 reaction equation
C(OC(=O)[NH:7][C:8]1[O:9][CH2:10][C@@:11]2([N:36]=1)[C:20]1([CH2:23][O:22][CH2:21]1)[C:19]([CH3:25])([CH3:24])[O:18][C:17]1[C:12]2=[CH:13][C:14]([NH:26][C:27]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][N:30]=2)=[O:28])=[CH:15][CH:16]=1)(C)(C)C>C1(C)C=CC=CC=1>[NH2:7][C:8]1[O:9][CH2:10][C@@:11]2([N:36]=1)[C:20]1([CH2:21][O:22][CH2:23]1)[C:19]([CH3:24])([CH3:25])[O:18][C:17]1[C:12]2=[CH:13][C:14]([NH:26][C:27]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][N:30]=2)=[O:28])=[CH:15][CH:16]=1

Participants

3

Reactant 1

HCID 86724284HCID 86724284, compound

Product 1

HCID 72202470HCID 72202470, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of tert-butyl[(4S)-6′-{[(5-chloropyridin-2-yl)carbonyl]amino}-2′,2′-dimethyldispiro[1,3-oxazole-4,4′-chromene-3′,3″-oxetan]-2-yl]carbamate (1.02 g, 1.93 mmol), silica gel (neutral; 3.06 g) and toluene (20.4 mL) was stirred for 3 hours at 120° C. The reaction mixture was cooled down to ambient temperature and concentrated at reduced pressure. The residue was purified with column chromatography on silica gel (CHCl3-EtOH, a linear gradient of EtOH from 0 to 15%) and then with NH-silica gel (Hexane-EtOAc, a linear gradient of EtOAc from 50 to 100%). The purified product was recrystallized from EtOH/H2O (1:1), and the solid was collected by filtration and dried at reduced pressure to give a hydrate of N-[(4S)-2-amino-2′,2′-dimethyldispiro[1,3-oxazole-4,4′-chromene-3′,3″-oxetan]-6′-yl]-5-chloropyridine-2-carboxamide (547 mg) as a crystal.

Workup

  1. temperatureThe reaction mixture was cooled down to ambient temperature
  2. concentrationconcentrated at reduced pressure
  3. customThe residue was purified with column chromatography on silica gel (CHCl3-EtOH
  4. customThe purified product was recrystallized from EtOH/H2O (1:1)
  5. filtrationthe solid was collected by filtration
  6. customdried at reduced pressure

Sources & evidence

ORD record
ord-c49dddfc7ab440f6965cd948dfa27aad
Source dataset
uspto-grants-2016_01
Patent number
US09242973B2

Reaction notes

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