3-(2-Amino-4-chloro-phenoxy)-benzamide → 3-[4-Chloro-2-(7-propyl-[1,8]naphthyridin-4-ylamino)-phenoxy]-benzamide

HRID 2358752Notes

Reaction equation

HRID 2358752 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.[NH2:15][C:16]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:17]=1[O:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22]([NH2:24])=[O:23]>C(O)C>[Cl:32][C:30]1[CH:29]=[CH:28][C:17]([O:18][C:19]2[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=2)[C:22]([NH2:24])=[O:23])=[C:16]([NH:15][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:31]=1

Participants

4

Reactant 2

HCID 284018643-(2-Amino-4-chloro-phenoxy)-benzamideHCID 441401765-Chloro-2-propyl-[1,8]naphthyridine

Product 1

HCID 684580573-[4-Chloro-2-(7-propyl-[1,8]naphthyridin-4-ylamino)-phenoxy]-benzamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Example 2g (140 mg, 0.68 mmol) was reacted with the product from Example 171b (178 mg, 0.68 mmol) in ethanol (5 mL) at 85° C. in a sealed tube for 18 h giving the crude title compound which was purified by HPLC with TFA providing the product as the trifluoroacetic acid (110 mg, 30%). 1H NMR (500 MHz, DMSO-d6) δ ppm: 8.81 (d, J=8.54 Hz, 1 H) 8.45 (d, J=7.32 Hz, 1 H) 6.76-6.79 (m, 2 H) 6.64 (d, J=8.54 Hz, 2 H) 6.44 (s, 1 H) 6.37 (t, J=7.93 Hz, 1 H) 6.31 (d, J=8.54 Hz, 1 H) 7.16 (dd, J=7.93, 2.44 Hz, 1 H) 6.84 (d, J=7.32 Hz, 1 H) 2.95 (t, J=7.32 Hz, 2 H) 1.80 (m, 2 H) 0.95 (t, J=7.32 Hz, 3 H); MS (ESI+) m/z 433 (M+H)+.

Sources & evidence

ORD record
ord-73bcbd96993141608ece6d40f9195ece
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

Loading…