Chloroform → HCID 67156151, compound

HRID 549167Notes

Reaction equation

HRID 549167 reaction equation
Cl[C:2]1[C:7]2[N:8]=[C:9]3[N:14]([C:6]=2[C:5]([CH3:16])=[C:4]([CH3:17])[N:3]=1)[C@@H:13]([CH3:15])[CH2:12][O:11][CH2:10]3.[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH2:25])=[CH:22][CH:21]=1.Cl.N1C=CC=CC=1.C(Cl)(Cl)Cl>FC(F)(F)CO>[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH:25][C:2]2[C:7]3[N:8]=[C:9]4[N:14]([C:6]=3[C:5]([CH3:16])=[C:4]([CH3:17])[N:3]=2)[C@@H:13]([CH3:15])[CH2:12][O:11][CH2:10]4)=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 754524-MethoxybenzylamineHCID 10176127Pyridinium chlorideHCID 86624131HCID 86624131, compound

Product 1

HCID 67156151HCID 67156151, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 64092,2,2-TrifluoroethanolSolvent

Conditions

Temperature
160 °C

Procedure

A conical microwave vial was charged with a solution of (4S)-9-chloro-4,6,7-trimethyl-3,4-dihydro-1H-pyrido[3′,4′:4,5]imidazo[2,1-c][1,4]oxazine (270 mg, 1.07 mmol) dissolved in 3.5 mL of 2,2,2-trifluoroethanol. 4-Methoxybenzylamine (1.4 mL, 10.7 mmol) and pyridine hydrochloride (620 mg, 5.35 mmol) were added and the vial was sealed. The solution was heated in an Emrys Optimizer microwave (Personal Chemistry) at 160° C. for 120 minutes. The solvent was removed under reduced pressure, and the resulting residue was partitioned between 20 mL of CH2Cl2 and 20 mL of 10% aqueous Na2CO3. The layers were separated, and the organic portion was washed with 10% aqueous Na2CO3 solution and brine, dried over Na2SO4, filtered and concentrated under reduced pressures to give a crude oil. Chromatography (SiO2, 0-20% CMA/CHCl3) afforded (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) as an orange syrup.

Workup

  1. customthe vial was sealed
  2. customThe solvent was removed under reduced pressure
  3. customthe resulting residue was partitioned between 20 mL of CH2Cl2 and 20 mL of 10% aqueous Na2CO3
  4. customThe layers were separated
  5. washthe organic portion was washed with 10% aqueous Na2CO3 solution and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressures
  9. customto give a crude oil

Sources & evidence

ORD record
ord-84021b4f78a44e8d8d88e10c53382685
Source dataset
uspto-grants-2011_05
Patent number
US07943609B2

Reaction notes

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