5-Chloro-2-methyl-1,8-naphthyridine → HCID 68460815, compound

HRID 2197743Notes

Reaction equation

HRID 2197743 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])[C:17]([OH:21])=[CH:16][C:15]=1[S:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:32])[CH3:31])=[CH:25][CH:24]=1>C(O)C>[OH:21][C:17]1[C:18]([CH3:20])=[CH:19][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)=[C:15]([S:22][C:23]2[CH:24]=[CH:25][C:26]([NH:29][C:30](=[O:32])[CH3:31])=[CH:27][CH:28]=2)[CH:16]=1

Participants

4

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridineHCID 60204797HCID 60204797, compound

Product 1

HCID 68460815HCID 68460815, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Example 1d (102 mg, 0.570 mmol) was reacted in ethanol (2 mL) with the product from Example 34b (161 mg, 0.560 mmol) for 18 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 (50 mg, 21%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.05 (s, 3H) 2.12 (s, 3H) 2.75 (s, 3H) 6.31 (d, J=6.99 Hz, 1H) 6.61 (s, 1H) 7.15 (s, 1H) 7.29 (d, J=8.46 Hz, 2H) 7.56 (d, J=8.82 Hz, 2H) 7.77 (d, J=8.82 Hz, 1H) 8.39 (d, J=5.52 Hz, 1H) 8.96 (d, J=8.82 Hz, 1H) 9.90 (s, 1H) 10.08 (s, 1H) 10.84 (s, 1H) 14.24 (br s, 1H); MS (ESI+) m/z 431 (M+H)+.

Sources & evidence

ORD record
ord-9eee533a5b5a4848917f0f81dce3e6c1
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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