5-Chloro-2-methyl-1,8-naphthyridine → HCID 68459957, compound

HRID 2358812Notes

Reaction equation

HRID 2358812 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:16]=[C:17]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:22]=2[NH2:28])[CH:18]=[CH:19][CH:20]=1>>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([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:18]=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridineHCID 68459498HCID 68459498, compound

Product 1

HCID 68459957HCID 68459957, compound

Procedure

The product from Example 1d (0.065 g, 0.36 mmol) was reacted with the product from Example 217b (0.072 g, 0.34 mmol) for 96 h at 100° C. following the procedure from Example 1g giving the crude title compound which was purified by HPLC with TFA providing a trifluoroacetic acid salt (0.102 gm, 64%). 1H NMR (300 MHz, DMSO-d6) ppm: 2.43 (s, 3 H) 2.72 (s, 3 H) 3.62 (s, 3 H) 6.29 (d, J=7.35 Hz, 1 H) 6.77 (dd, J=7.91, 2.02 Hz, 1 H) 6.87-7.00 (m, 2 H) 7.17 (t, J=7.91 Hz, 1 H) 7.36 (s, 1 H) 7.41-7.46 (m, 1 H) 7.51-7.56 (m, 1 H) 7.75 (d, J=8.46 Hz, 1 H) 8.32 (d, J=7.35 Hz, 1 H) 8.91 (d, J=8.82 Hz, 1 H) 11.99-12.22 (s, 1 H); MS (ESI+) m/z 356.0 (M+H)+; (ESI−) m/z 354.0 (M−H)−.

Sources & evidence

ORD record
ord-e7ad7450d91d40319df6795b38d56b31
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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