5-Chloro-2-methyl-1,8-naphthyridine → HCID 68459604, compound

HRID 2358810Notes

Reaction equation

HRID 2358810 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:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=1[C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:30])[CH3:29])=[CH:23][CH:22]=1>>[CH3:20][C:18]1[CH:17]=[CH:16][C:15]([C:21]2[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:30])[CH3:29])=[CH:23][CH:22]=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:19]=1

Participants

3

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridineHCID 68459639HCID 68459639, compound

Product 1

HCID 68459604HCID 68459604, compound

Procedure

The product from Example 1d (0.041 g, 0.23 mmol) was reacted with the product from Example 215b (0.062 g, 0.23 mmol) for 46 h at 100° C. 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 salt (0.073 g, 60%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 1.98 (s, 3 H) 2.42 (s, 3 H) 2.72 (s, 3 H) 6.28 (d, J=6.99 Hz, 1 H) 7.27-7.56 (m, 7 H) 7.74 (d, J=8.46 Hz, 1 H) 8.33 (d, J=7.35 Hz, 1 H) 8.94 (d, J=8.82 Hz, 1 H) 9.95 (s, 1 H) 11.06 (s, 1 H); MS (ESI+) m/z 383.1 (M+H)+, (ESI−) m/z 381.1 (M−H)−.

Sources & evidence

ORD record
ord-6c8f89ea3b0e426eb7a0c26b230bbb36
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

Loading…