Water → [1,2,4]Triazolo[5,1-f][1,6]naphthyridine-2-carbaldehyde

HRID 1615655Notes

Reaction equation

Cl[CH:2](Cl)[C:3]1[N:15]=[C:6]2[C:7]3[CH:8]=[CH:9][CH:10]=[N:11][C:12]=3[CH:13]=[CH:14][N:5]2[N:4]=1.[OH2:17]>CNC>[N:15]1[C:3]([CH:2]=[O:17])=[N:4][N:5]2[CH:14]=[CH:13][C:12]3[N:11]=[CH:10][CH:9]=[CH:8][C:7]=3[C:6]=12

Participants

Conditions

Temperature: 70 °C

Procedure

A microwave tube was charged with a mixture of 2-(dichloromethyl)-[1,2,4]triazolo[5,1-f][1,6]naphthyridine (180 mg, 0.71 mmol) in dimethylamine in water (5 mL, 33% wt in water) and heated at 70° C. in oil bath for 5 h, and then cooled to room temperature. The mixture was extracted with EtOAc (3×20 mL). The combined organic layer was dried over Na2SO4, filtered, and concentrated. The residue was purified by silica gel column chromatography (eluting with DCM/MeOH v/v 100/1 and 50/1) to yield [1,2,4]triazolo[5,1-f][1,6]naphthyridine-2-carbaldehyde as a white solid (85 mg, yield 60%). ESI MS: m/z 199 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 10.22 (s, 1H), 9.06 (m, 1H), 8.97 (m, 1H), 8.56 (d, J=7.2 Hz, 1H), 7.65 (m, 2H).

Workup

temperaturecooled to room temperature
extractionThe mixture was extracted with EtOAc (3×20 mL)
dry with materialThe combined organic layer was dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica gel column chromatography (
washeluting with DCM/MeOH v/v 100/1 and 50/1)

Sources & evidence

ORD record: ord-3edc93cba87748f3a182ec2d54a7b18d
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765760B2

Reaction notes

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