5-Chloro-2-phenoxyaniline → (5-Chloro-2-phenoxy-phenyl)-[1,6]naphthyridin-5-yl-amine

HRID 883909

Reaction equation

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

Participants

Reactant 2

HCID 667385-Chloro-2-phenoxyaniline

HCID 122042345-Chloro-1,6-naphthyridine

Product 1

HCID 67249138(5-Chloro-2-phenoxy-phenyl)-[1,6]naphthyridin-5-yl-amine

Procedure

The product from Example 36e (0.040 g, 0.24 mmol) was reacted with 5-chloro-2-phenoxy-phenylamine as (0.048 g, 0.24 mmol) for 48 h at 100° C. following the procedure from Example 7g giving the crude title compound which was purified by HPLC with TFA providing the product as a trifluoroacetic acid salt (0.046 g, 40%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 6.96 (d, J=7.35 Hz, 2 H) 7.00-7.10 (m, 2 H) 7.22-7.39 (m, 4 H) 7.66 (dd, J=8.46, 4.41 Hz, 1 H) 7.91 (d, J=1.84 Hz, 1 H) 8.07 (d, J=6.25 Hz, 1 H) 8.76 (d, J=8.46 Hz, 1 H) 9.07 (d, J=3.31 Hz, 1 H); MS (ESI+) m/z 348.0 (M+H)+; (ESI−) m/z 346.1 (M−H)−.

Sources & evidence

ORD record: ord-3868cea8a7764d0fb052e4eda88633c6
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236950B2

Linked notes

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