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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2197839Generated: October 26, 2026

5-Chloro-2-methyl-1,8-naphthyridine → 4-(4-Methyl-2-(7-methyl-1,8-naphthyridin-4-ylamino)phenoxy)phenol

https://huagongshe.com/reaction/2197839

Reaction equation

Participants

RoleNameHCIDCharge
Reactant5-Chloro-2-methyl-1,8-naphthyridineHCID 12266372—
Reactant4-(2-Amino-4-methylphenoxy)phenolHCID 66808388—
Product4-(4-Methyl-2-(7-methyl-1,8-naphthyridin-4-ylamino)phenoxy)phenolHCID 68459283—

Reaction Steps

The product from Example 1d (278 mg, 1.56 mmol) was reacted with the product from Example 122b (336 mg, 1.56 mmol) for 18 h following the procedure from Example 1g giving the crude title compound which was purified by HPLC with TFA providing the product as a trifluoroacetic acid (226 mg, 31%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.34 (s, 3H) 2.74 (s, 3H) 6.56 (d, J=6.99 Hz, 1H) 6.64-6.71 (m, 2H) 6.75-6.81 (m, 2H) 6.89 (d, J=8.46 Hz, 1H) 7.26 (dd, J=8.46, 1.84 Hz, 1H) 7.31 (s, 1H) 7.76 (d, J=8.82 Hz, 1H) 8.48 (d, J=6.99 Hz, 1H) 8.95 (d, J=8.46 Hz, 1H) 9.34 (s, 1H) 10.91 (s, 1H) 14.36 (s, 1H); MS (ESI+) m/z 358 (M+H−TFA)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08338605B2
Source datasetuspto-grants-2012_12
ORD IDord-3b171cda54d54203b3395361e3c53a9c
Source noteuspto-grants-2012_12