Chloroform → HCID 58406181, compound

HRID 221600Notes

Reaction equation

HRID 221600 reaction equation
COC1C=CC(C[NH:8][C:9]2[C:14]3[N:15]=[C:16]4[N:21]([C:13]=3[C:12]([CH3:23])=[C:11]([CH3:24])[N:10]=2)[C@@H:20]([CH3:22])[CH2:19][O:18][CH2:17]4)=CC=1.[OH-].[Na+].C(Cl)(Cl)Cl>FC(F)(F)C(O)=O>[CH3:22][C@H:20]1[CH2:19][O:18][CH2:17][C:16]2=[N:15][C:14]3[C:9]([NH2:8])=[N:10][C:11]([CH3:24])=[C:12]([CH3:23])[C:13]=3[N:21]12

Participants

5

Reactant 3

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 67156151HCID 67156151, compound

Product 1

HCID 58406181HCID 58406181, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(4S)—N-(4-Methoxybenzyl)-4,6,7-trimethyl-3,4-dihydro-1H-pyrido[3′,4′:4,5]imidazo[2,1-c][1,4]oxazin-9-amine (350 mg, 0.99 mmol) was dissolved in 15 mL of trifluoroacetic acid and stirred at ambient temperature overnight. The solvent was removed under reduced pressure to give an orange residue which was then treated with 30 mL of aqueous 10% NaOH solution and the mixture was stirred for 2 hours. The solution was then extracted with CH2Cl2 (3×30 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give an orange solid. Chromatography (SiO2, 10-30% CMA/CHCl3) gave an off-white solid. Crystallization from acetonitrile gave (4S)-4,6,7-trimethyl-3,4-dihydro-1H-pyrido[3′,4′:4,5]imidazo[2,1-c][1,4]oxazin-9-amine (115 mg) as a white powder, mp 264-267° C.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customto give an orange residue which
  3. stirringthe mixture was stirred for 2 hours
  4. extractionThe solution was then extracted with CH2Cl2 (3×30 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto give an orange solid
  10. customCrystallization from acetonitrile

Sources & evidence

ORD record
ord-caadab2dd26a4307b7de3141516a5242
Source dataset
uspto-grants-2012_06
Patent number
US08207162B2

Reaction notes

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