5-Chloro-2-methyl-1,8-naphthyridine → HCID 68459000, compound

HRID 2197974Notes

Reaction equation

HRID 2197974 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.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:22]=2[NH2:28])=[CH:17][CH:16]=1>>[CH3:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:22]=2[NH:28][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][CH:20]=1

Participants

3

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridineHCID 68456258HCID 68456258, compound

Product 1

HCID 68459000HCID 68459000, compound

Procedure

The product from Example 1d (0.088 g, 0.49 mmol) was reacted with the product from Example 214b (107 mg, 0.49 mmol) for 65 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 salt (0.106 g, 45%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.41 (s, 3H) 2.72 (s, 3H) 3.66 (s, 3H) 6.29 (d, J=6.99 Hz, 1H) 6.84 (d, J=8.82 Hz, 2H) 7.27-7.53 (m, 5H) 7.75 (d, J=8.46 Hz, 1H) 8.32 (d, J=6.99 Hz, 1H) 8.90 (d, J=8.46 Hz, 1H) 10.88-11.05 (m, 1H); MS (ESI+) m/z 356.0 (M+H)+; (ESI−) m/z 354.1 (M−H)−.

Sources & evidence

ORD record
ord-980ac24ef6d54ebdb1afe4c3a5f74452
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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