5-Chloro-2-methyl-1,8-naphthyridine → HCID 68461520, compound

HRID 2358663Notes

Reaction equation

HRID 2358663 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]([Br:20])[CH:17]=[CH:16][C:15]=1[S:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:31])[CH3:30])=[CH:24][CH:23]=1>C(O)C>[Br:20][C:18]1[CH:17]=[CH:16][C:15]([S:21][C:22]2[CH:23]=[CH:24][C:25]([NH:28][C:29](=[O:31])[CH3:30])=[CH:26][CH:27]=2)=[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:19]=1

Participants

4

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridineHCID 28401654HCID 28401654, compound

Product 1

HCID 68461520HCID 68461520, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Example 1d (106 mg, 0.59 mmol) was reacted in ethanol (2 mL) with the product from Example 106b (200 mg, 0.59 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 (53 mg, 19%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.05 (s, 3 H) 2.77 (s, 3H), 6.41 (d, J=6.99 Hz, 1 H), 7.02 (d, J=8.82 Hz, 1 H), 7.33 (d, J=8.46 Hz, 2 H), 7.58 (d, J=8.82 Hz, 2H), 7.65 (dd, J=8.46, 2.21 Hz, 1 H) 7.77 (d, J=2.21 Hz, 1 H), 7.81 (d, J=8.82 Hz, 1 H), 8.48 (d, J=6.99 Hz, 1 H), 8.96 (d, J=8.82 Hz, 1 H), 10.11 (s, 1 H), 11.06 (s, 1 H), 14.53 (s, 1 H); MS (DCI/NH3) m/z 479 (M+H)+.

Sources & evidence

ORD record
ord-6dd835cc82364c1a91c0fc01b4d245eb
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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