5-Chloro-2-methyl-1,8-naphthyridine → HCID 68457711, compound

HRID 2358637Notes

Reaction equation

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

Participants

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridine

HCID 68460819HCID 68460819, compound

Product 1

HCID 68457711HCID 68457711, compound

Procedure

The product from Example 85b (0.277 g, 1.05 mmol) was reacted with the product from Example 1d (0.09 g, 0.504 mmol) for 41 h following the procedure from Example 1g giving the crude title compound which was purified by HPLC with TFA providing the product as the trifluoroacetic acid salt (0.078 g, 28%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.41 (s, 3H) 2.70-2.82 (m, 6H) 6.36 (d, J=6.99 Hz, 1H) 7.20 (d, J=8.46 Hz, 2H) 7.35-7.45 (m, 2H) 7.51 (d, 1H) 7.64 (d, J=8.46 Hz, 2H) 7.75 (d, J=8.82 Hz, 1H) 8.33-8.45 (m, 2H) 8.90 (d, J=8.82 Hz, 1H) 11.03 (s, 1H); MS (ESI+) m/z 415.0 (M+H)+; (ESI−) m/z 413.1 (M−H)−.

Sources & evidence

ORD record: ord-df813fe34f0446f7b9a719ff60aa8830
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07763731B2

Reaction notes

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