Trichloroacetyl isocyanate → 9,10-dihydro-8H-[1,2]oxazino[2',3':1,2]imidazo[4,5-c]-1,5-naphthyridin-6-amine

HRID 415521Notes

Reaction equation

HRID 415521 reaction equation
[N:1]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:2]=1[C:3]1[N:14]3[O:15][CH2:16][CH2:17][CH2:18][C:13]3=[N:12][C:4]=1[CH:5]=[N+:6]2[O-].ClC(Cl)(Cl)C([N:23]=C=O)=O>ClCCl>[N:1]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:2]=1[C:3]1[N:14]3[O:15][CH2:16][CH2:17][CH2:18][C:13]3=[N:12][C:4]=1[C:5]([NH2:23])=[N:6]2

Participants

4

Reactant 2

HCID 76400Trichloroacetyl isocyanateHCID 666198439,10-dihydro-8H-[1,2]oxazino[2',3':1,2]imidazo[4,5-c][1,5]naphthyridine 5-oxide

Product 1

HCID 248521739,10-dihydro-8H-[1,2]oxazino[2',3':1,2]imidazo[4,5-c]-1,5-naphthyridin-6-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 9,10-dihydro-8H-[1,2]oxazino[2′,3′:1,2]imidazo[4,5-c][1,5]naphthyridine 5-oxide (0.13 g, 0.54 mmol) in dichloromethane (10 mL) was added trichloroacetyl isocyanate (0.08 mL, 0.67 mmol). After 1.5 hours, the solution was concentrated under reduced pressure and methanol (4 mL) and sodium methoxide (2 drops of a 25% w/w solution in methanol) were added with stirring. After 18 hours the solution was concentrated under reduced pressure. The resulting solid was recrystallized from methanol/ethyl acetate to provide 9,10-dihydro-8H-[1,2]oxazino[2′,3′:1,2]imidazo[4,5-c]-1,5-naphthyridin-6-amine.

Workup

  1. concentrationthe solution was concentrated under reduced pressure and methanol (4 mL) and sodium methoxide (2 drops of a 25% w/w solution in methanol)
  2. additionwere added
  3. concentrationAfter 18 hours the solution was concentrated under reduced pressure
  4. customThe resulting solid was recrystallized from methanol/ethyl acetate

Sources & evidence

ORD record
ord-e79846fa95724ff8af873d1c2f4836c3
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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