1-{[(3-Nitro[1,5]naphthyridin-4-yl)amino]methyl}cyclohexanol → 1-{[(3-Amino[1,5]naphthyridin-4-yl)amino]methyl}cyclohexanol

HRID 44741Notes

Reaction equation

HRID 44741 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][C:16]1([OH:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)=[N:11][CH:10]=[CH:9][CH:8]=2)([O-])=O>[Pt].C(#N)C>[NH2:1][C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][C:16]1([OH:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)=[N:11][CH:10]=[CH:9][CH:8]=2

Participants

4

Reactant 1

HCID 574578211-{[(3-Nitro[1,5]naphthyridin-4-yl)amino]methyl}cyclohexanol

Product 1

HCID 574578221-{[(3-Amino[1,5]naphthyridin-4-yl)amino]methyl}cyclohexanol

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-{[(3-nitro[1,5]naphthyridin-4-yl)amino]methyl}cyclohexanol (4.55 g, 15.1 mmol) and 5% platinum on carbon (0.50 g) in acetonitrile (100 mL) was hydrogenated at 50 psi (3.5×105 Pa) overnight on a Parr apparatus. The reaction mixture was filtered through CELITE filter agent, which was rinsed with methanol afterwards. The filtrate was concentrated to give 1-{[(3-amino[1,5]naphthyridin-4-yl)amino]methyl}cyclohexanol. The 1-{[(3-amino[1,5]naphthyridin-4-yl)amino]methyl}cyclohexanol was concentrated from chloroform several times to remove residual methanol and was used directly onto the next step.

Workup

  1. customwas hydrogenated at 50 psi (3.5×105 Pa) overnight on a Parr apparatus
  2. filtrationThe reaction mixture was filtered through CELITE
  3. filtrationfilter agent, which
  4. washwas rinsed with methanol afterwards
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-b250780443984b3d86370bce76de5511
Source dataset
uspto-grants-2013_09
Patent number
US08541438B2

Reaction notes

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