5-Bromo-2-phenoxyaniline → N-(5-bromo-2-phenoxyphenyl)-7-propyl-1,8-naphthyridin-4-amine

HRID 2358678Notes

Reaction equation

HRID 2358678 reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:12][CH2:13][CH3:14])=[N:7]2.[Br:15][C:16]1[CH:17]=[CH:18][C:19]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:20]([NH2:22])[CH:21]=1>>[Br:15][C:16]1[CH:17]=[CH:18][C:19]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:20]([NH:22][C:2]2[C:3]3[C:8](=[N:7][C:6]([CH2:12][CH2:13][CH3:14])=[CH:5][CH:4]=3)[N:9]=[CH:10][CH:11]=2)[CH:21]=1

Participants

3

Reactant 2

HCID 161094555-Bromo-2-phenoxyanilineHCID 441401765-Chloro-2-propyl-[1,8]naphthyridine

Product 1

HCID 68460728N-(5-bromo-2-phenoxyphenyl)-7-propyl-1,8-naphthyridin-4-amine

Procedure

The product from Example 2g (275 mg, 1.33 mmol) was reacted with the product from Example 124b (351 mg, 1.33 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 (470 mg, 65%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 0.95 (t, J=7.35 Hz, 3 H) 1.72-1.93 (m, 2 H) 2.91-3.02 (m, 2 H) 6.70 (d, J=6.99 Hz, 1 H) 6.97 (d, J=7.72 Hz, 2 H) 7.10 (t, J=8.27 Hz, 2 H) 7.27-7.36 (m, 2 H) 7.68 (dd, J=8.82, 2.57 Hz, 1 H) 7.78 (d, J=8.46 Hz, 1 H) 7.82 (d, J=2.57 Hz, 1 H) 8.52 (d, J=6.99 Hz, 1 H) 8.89 (d, J=8.82 Hz, 1 H) 10.90 (s, 1 H) 14.49 (s, 1 H); MS (ESI+) m/z 436 (M+H−TFA)+.

Sources & evidence

ORD record
ord-28c7e9d4415d48dabd2e89e72fe58322
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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