Ethyl isothiocyanate → 1-Ethyl-3-[7-(3,4,5-trimethoxy-phenylamino)-[1,5]naphthyridin-2-yl]-thiourea

HRID 1256187Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:13][C:14]2[CH:23]=[C:22]3[C:17]([CH:18]=[CH:19][C:20]([NH2:24])=[N:21]3)=[N:16][CH:15]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[CH2:25]([N:27]=[C:28]=[S:29])[CH3:26]>N1C=CC=CC=1>[CH2:25]([NH:27][C:28]([NH:24][C:20]1[CH:19]=[CH:18][C:17]2[C:22](=[CH:23][C:14]([NH:13][C:5]3[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)=[CH:15][N:16]=2)[N:21]=1)=[S:29])[CH3:26]

Participants

Conditions

Temperature: 140 °C

Procedure

In a sealed reactor, 88 mg (269 μmol, 1 eq) of N*7*-(3,4,5-trimethoxy-phenyl)-[1,5]naphthyridine-2,7-diamine and 48 μL (538 μmol, 2 eq) of ethyl isothiocyanate were introduced in 3 mL of pyridine. The mixture was stirred at 140° C. for 24 h. The mixture was allowed to reach rt and the solvent was removed under reduced pressure. The residue was purified by column chromatography using methylene chloride/ethanol: 96/4 as eluent. The solvent was evaporated to dryness to afford 56 mg of yellow powder with 51% yield.

Workup

customto reach rt
customthe solvent was removed under reduced pressure
customThe residue was purified by column chromatography
customThe solvent was evaporated to dryness

Sources & evidence

ORD record: ord-14781fcdda93495ab922f642a1b6b3ed
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461178B2

Reaction notes

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