alpha-Methyl-DL-leucine → 1-[4-(9-Phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]methanamine

HRID 1678741Notes

Reaction equation

[C:1]1([C:7]2[C:8]([C:20]3[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=3)=[N:9][C:10]3[CH:11]=[CH:12][N:13]4[CH:19]=[N:18][N:17]=[C:14]4[C:15]=3[CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:28]C(C)(CC(C)C)C(O)=O>CN(C=O)C>[C:1]1([C:7]2[C:8]([C:20]3[CH:27]=[CH:26][C:23]([CH2:24][NH2:28])=[CH:22][CH:21]=3)=[N:9][C:10]3[CH:11]=[CH:12][N:13]4[CH:19]=[N:18][N:17]=[C:14]4[C:15]=3[CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A suspension of 4-(9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzaldehyde (4-2, 0.80 g, 2.3 mmol) and 2-amino-2,4-dimethylpentanoic acid (3-7, 0.340 g, 2.3 mmol) in DMF (10 mL) was heated at 150° C. for 30 min. The reaction mixture cooled and the solvent was removed in vacuo. The crude residue was dissolved in 3N HCl (8 mL) and was heated at 100° C. for 30 min. The mixture was cooled and purified via reverse phase HPLC (5-65% acetonitrile/water over 15 min) to give, upon evaporation of the solvents, the title compound as a yellow solid. 1H-NMR (CD3OD) δ 9.60 (s, 1H), 8.98 (s, 1H), 8.73 (d, 1H), 7.75 (d, 1H), 7.60 (d, 2H), 7.46 (d, 2H), 7.39-7.36 (m, 5H), 4.15 (s, 2H).

Workup

temperatureThe reaction mixture cooled
customthe solvent was removed in vacuo
dissolutionThe crude residue was dissolved in 3N HCl (8 mL)
temperaturewas heated at 100° C. for 30 min
temperatureThe mixture was cooled
custompurified via reverse phase HPLC (5-65% acetonitrile/water over 15 min)
customto give, upon evaporation of the solvents

Sources & evidence

ORD record: ord-7272b19634b34dbba4e62781cb50c2fa
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008317B2

Reaction notes

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