5-Chloro-2-methyl-1,8-naphthyridine → 4-(4-chloro-2-(7-methyl-1,8-naphthyridin-4-ylamino)phenoxy)-N-propylbenzamide

HRID 2358688Notes

Reaction equation

HRID 2358688 reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:12])=[N:7]2.[NH2:13][C:14]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:15]=1[O:16][C:17]1[CH:28]=[CH:27][C:20]([C:21]([NH:23][CH2:24][CH2:25][CH3:26])=[O:22])=[CH:19][CH:18]=1>>[Cl:33][C:31]1[CH:30]=[CH:29][C:15]([O:16][C:17]2[CH:28]=[CH:27][C:20]([C:21]([NH:23][CH2:24][CH2:25][CH3:26])=[O:22])=[CH:19][CH:18]=2)=[C:14]([NH:13][C:2]2[C:3]3[C:8](=[N:7][C:6]([CH3:12])=[CH:5][CH:4]=3)[N:9]=[CH:10][CH:11]=2)[CH:32]=1

Participants

3

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridineHCID 684596204-(2-amino-4-chlorophenoxy)-N-propylbenzamide

Product 1

HCID 684583624-(4-chloro-2-(7-methyl-1,8-naphthyridin-4-ylamino)phenoxy)-N-propylbenzamide

Procedure

The product from Example 1d (111 mg, 0.62 mmol) was reacted with the product from Example 127b (190 mg, 0.62 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 (45.9 mg, 13%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 0.86 (t, J=7.54 Hz, 3 H) 1.39-1.60 (m, 2 H) 2.72 (s, 3 H) 3.08-3.26 (m, 2 H) 6.72 (d, J=6.99 Hz, 1 H) 6.96 (d, J=8.82 Hz, 2H) 7.29 (d, J=8.82 Hz, 1 H) 7.61 (dd, J=8.82, 2.57 Hz, 1 H) 7.69-7.80 (m, 4 H) 8.34 (t, J=5.52 Hz, 1H) 8.53 (d, J=6.99 Hz, 1 H) 8.82 (d, J=8.46 Hz, 1 H) 10.91 (s, 1 H) 14.55 (s, 1H); MS (ESI+) m/z 447 (M+H−TFA)+.

Sources & evidence

ORD record
ord-6df120619af143768900fef3cd577ebc
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

Loading…