5-Chloro-2-phenoxyaniline → (5-Chloro-2-phenoxy-phenyl)-(7-trifluoromethyl-[1,8]naphthyridin-4-yl)-amine

HRID 2358591Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:6]([NH2:8])[CH:7]=1.Cl[C:17]1[CH:26]=[CH:25][N:24]=[C:23]2[C:18]=1[CH:19]=[CH:20][C:21]([C:27]([F:30])([F:29])[F:28])=[N:22]2>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:6]([NH:8][C:17]2[C:18]3[C:23](=[N:22][C:21]([C:27]([F:30])([F:29])[F:28])=[CH:20][CH:19]=3)[N:24]=[CH:25][CH:26]=2)[CH:7]=1

Participants

Reactant 2

HCID 667385-Chloro-2-phenoxyaniline

HCID 222852765-chloro-2-(trifluoromethyl)-1,8-Naphthyridine

Product 1

HCID 68461407(5-Chloro-2-phenoxy-phenyl)-(7-trifluoromethyl-[1,8]naphthyridin-4-yl)-amine

Procedure

The product from Example 42b (60 mg, 0.27 mmol) was reacted with the product from Example 7d (63 mg, 0.27 mmol) for 24 h following the procedure from Example 1g giving the crude title compound as a solid which was triturated with 4:1 ether/THF giving the product as a hydrochloride salt (112 mg, 91%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 6.82 (d, J=6.99 Hz, 1H) 6.98 (d, J=7.72 Hz, 2H) 7.13 (m, 2H) 7.32 (dd, J=7.73 Hz, J=8.82 Hz, 2H) 7.57 (dd, J=2.57 Hz, J=8.82 Hz, 1H) 7.71 (d, J=2.57 Hz, 1H) 8.36 (d, J=8.82 Hz, 1H) 8.69 (d, J=6.99 Hz, 1H) 9.42 (d, J=8.82 Hz, 1H) 11.47 (br s, 1H) 14.40 (br s, 1H); MS (ESI+) m/z 416 (M−Cl)+; (ESI−) m/z 414 (M−HCl)−.

Sources & evidence

ORD record: ord-bfc678c21b3d424483b2345048f4495a
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07763731B2

Reaction notes

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