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

HRID 1678744Notes

Reaction equation

[CH3:1][C:2]1[N:14]2[C:5]([C:6]3[CH:7]=[C:8]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:9]([C:15]4[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=4)=[N:10][C:11]=3[CH:12]=[CH:13]2)=[N:4][N:3]=1.[NH2:29]C(C)(CC(C)C)C(O)=O>CN(C=O)C>[CH3:1][C:2]1[N:14]2[C:5]([C:6]3[CH:7]=[C:8]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:9]([C:15]4[CH:22]=[CH:21][C:18]([CH2:19][NH2:29])=[CH:17][CH:16]=4)=[N:10][C:11]=3[CH:12]=[CH:13]2)=[N:4][N:3]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A suspension of 4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzaldehyde (13, 0.25 g, 0.69 mmol) and 2-amino-2,4-dimethylpentanoic acid (3-7, 0.101 g, 0.69 mmol) in DMF (3 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 (2.5 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. HRMS m/z (M+1) Calcd: 366.1713. Found 366.1715.

Workup

temperatureThe reaction mixture cooled
customthe solvent was removed in vacuo
dissolutionThe crude residue was dissolved in 3N HCl (2.5 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-fb4fe4861f764e7c8c41baa918afdfa4
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008317B2

Reaction notes

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