Chloroform → HCID 67156151, compound

HRID 221599Notes

Reaction equation

HRID 221599 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-2657f413b63e41c2abb981908e284275
Source dataset
uspto-grants-2012_06
Patent number
US08207162B2

Reaction notes

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