5-Chlorotetrazolo(1,5-a][1,7]naphthyridine → HCID 12015801, compound

HRID 2181948Notes

Reaction equation

HRID 2181948 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][N:8]=[CH:9][CH:10]=2)[N:5]2[N:12]=[N:13][N:14]=[C:4]2[CH:3]=1>C(N)C(C)C>[CH3:10][CH:11]([CH3:2])[CH2:6][NH:5][C:2]1[C:11]2[C:6](=[CH:7][N:8]=[CH:9][CH:10]=2)[N:5]2[N:12]=[N:13][N:14]=[C:4]2[CH:3]=1

Participants

3

Reactant 1

HCID 120158005-Chlorotetrazolo(1,5-a][1,7]naphthyridine

Product 1

HCID 12015801HCID 12015801, compound

Reagents, catalysts & solvents 1

HCID 6558IsobutylamineSolvent

Procedure

A suspension of 5-chlorotetrazolo[1,5-a][1,7]naphthyridine (20 g) in isobutylamine (100 mL) was heated at reflux for several hours. The reaction mixture was concentrated under vacuum. The residue was taken up in dichloromethane, washed with water, dried over magnesium sulfate then concentrated under vacuum. The residue was recrystallized from toluene to give a material that was a mixture by thin layer chromatography. The material was purified by flash chromatography, silica gel eluting with dichloromethane, 5-20% ethyl acetate in dichloromethane, and 10% methanol in dichloromethane. The fractions with the slower moving material were concentrated to provide N5-(2-methylpropyl)tetrazolo[1,5-a][1,7]naphthyridin-5-amine as a solid, m.p. 220-221° C. Analysis: Calculated for C12H14N6: % C, 59.49; % H, 5.82; % N, 34.69; Found: % C, 59.35; % H, 5.89; % N, 34.88.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for several hours
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationthen concentrated under vacuum
  7. customThe residue was recrystallized from toluene
  8. customto give a material that
  9. customThe material was purified by flash chromatography, silica gel eluting with dichloromethane, 5-20% ethyl acetate in dichloromethane, and 10% methanol in dichloromethane
  10. concentrationwere concentrated

Sources & evidence

ORD record
ord-8045482f3a7545919288b2c4091c962d
Source dataset
uspto-grants-2005_05
Patent number
US06894165B2

Reaction notes

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