Hydrochloric Acid → HCID 50990950, compound

HRID 539645Notes

Reaction equation

HRID 539645 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][O:9][C:10]1[C:11]([Cl:34])=[CH:12][C:13]([CH3:33])=[C:14]([NH:16][C:17]2[N:25]3[C:20]([CH2:21][O:22][CH2:23][C@H:24]3[C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)=[N:19][N:18]=2)[CH:15]=1)(C)(C)C.Cl>CO>[Cl:34][C:11]1[CH:12]=[C:13]([CH3:33])[C:14]([NH:16][C:17]2[N:25]3[C:20]([CH2:21][O:22][CH2:23][C@H:24]3[C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)=[N:19][N:18]=2)=[CH:15][C:10]=1[O:9][CH2:8][CH2:7][OH:6]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58200308HCID 58200308, compound

Product 1

HCID 50990950HCID 50990950, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirring room temperature solution of {5-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-4-chloro-2-methyl-phenyl}-[(R)-5-(4-fluoro-phenyl)-5,6-dihydro-8H-[1,2,4]triazolo[3,4-c][1,4]oxazin-3-yl]-amine (700 mg, 1.31 mmol) in MeOH (20 mL) was added 6N aqueous HCl (1.5 mL). The mixture was stirred at room temperature for 10 minutes and then concentrated to dryness under reduced pressure. The residue was partitioned between saturated aqueous sodium carbonate and EtOAc. The organic layer was separated, washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was chromatographed through silica gel (MeOH/CH2Cl2/NH4OH 5%/74.75%/0.25%) to give 520 mg (95%) of 2-{2-Chloro-5-[(R)-5-(4-fluoro-phenyl)-5,6-dihydro-8H-[1,2,4]triazolo[3,4-c][1,4]oxazin-3-ylamino]-4-methyl-phenoxy}-ethanol, MP=161-162° C., MS (M+H)=420.

Workup

  1. concentrationconcentrated to dryness under reduced pressure
  2. customThe residue was partitioned between saturated aqueous sodium carbonate and EtOAc
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was chromatographed through silica gel (MeOH/CH2Cl2/NH4OH 5%/74.75%/0.25%)

Sources & evidence

ORD record
ord-3a4b42b8bf5e4173b1d8c8b3c261ce65
Source dataset
uspto-grants-2014_10
Patent number
US08871760B2

Reaction notes

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