5-Chloro-2-methyl-1,8-naphthyridine → HCID 68457776, compound

HRID 2358791Notes

Reaction equation

HRID 2358791 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:15]=[C:16]([CH:29]=[C:30]([Cl:32])[CH:31]=1)[O:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:28])[CH3:27])=[CH:21][CH:20]=1>>[Cl:32][C:30]1[CH:29]=[C:16]([CH:15]=[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:31]=1)[O:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:28])[CH3:27])=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridineHCID 68458724HCID 68458724, compound

Product 1

HCID 68457776HCID 68457776, compound

Procedure

The product from Example 1d (70 mg, 0.39 mmol) was reacted with the product from Example 197d (110 mg, 0.39 mmol) for 23 h following the procedure from Example 1g giving the crude title compound which was purified by trituration with EtOAc providing the title compound (140 mg, 82%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.05 (s, 3H), 2.75 (s, 3H), 5.11 (s, 2H), 6.90 (d, J=7.0 Hz, 1H), 7.12 (br-s, 1H), 7.17 (br-s, 2H), 7.38 (d, J=8.5 Hz, 2H), 7.61 (d, J=8.5 Hz, 2H), 7.78 (d, J=8.9 Hz, 1H), 8.50 (d, J=7.0 Hz, 1H), 9.12 (d, J=8.9 Hz, 1H), 10.06 (s, 1H), 11.17 (br-s, 1H); MS (ESI+) m/z 433, 435 (M+H)+, (ESI−) m/z 431, 433 (M−H)−.

Sources & evidence

ORD record
ord-2ffe52e448c948e79b7b97dcf0ed8009
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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