5-Chloro-2-methyl-1,8-naphthyridine → HCID 68461305, compound

HRID 2358723Notes

Reaction equation

HRID 2358723 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]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-:30])=[O:29])[CH:23]=2)[CH:17]=[CH:16][C:15]=1[S:31][C:32]1[CH:37]=[CH:36][C:35]([NH:38][C:39](=[O:41])[CH3:40])=[CH:34][CH:33]=1>C(O)C>[CH3:12][C:6]1[N:7]=[C:8]2[C:3]([C:2]([NH:13][C:14]3[CH:19]=[C:18]([O:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-:30])=[O:29])[CH:23]=4)[CH:17]=[CH:16][C:15]=3[S:31][C:32]3[CH:37]=[CH:36][C:35]([NH:38][C:39](=[O:41])[CH3:40])=[CH:34][CH:33]=3)=[CH:11][CH:10]=[N:9]2)=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridineHCID 68460917HCID 68460917, compound

Product 1

HCID 68461305HCID 68461305, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Example 1d (18 mg, 0.085 mmol) was reacted in ethanol (1 mL) with the product from Example 155a (34 mg, 0.085 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 (13 mg, 29%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 0.98 (t, J=7.35 Hz, 3H) 1.72-1.92 (m, 2 H) 2.02 (s, 3 H) 2.99 (t, J=7.54 Hz, 2 H) 5.32 (s, 2 H) 6.30 (d, J=6.99 Hz, 1 H) 7.15 (d, J=8.46 Hz, 2 H) 7.19-7.25 (m, 1 H) 7.27 (d, J=2.57 Hz, 1 H) 7.38 (d, J=8.82 Hz, 1 H) 7.43 (d, J=8.46 Hz, 2 H) 7.72 (t, J=7.91 Hz, 1 H) 7.81 (d, J=8.82 Hz, 1 H) 7.91 (d, J=7.72 Hz, 1 H) 8.22 (d, J=8.82 Hz, 1 H) 8.32 (s, 1 H) 8.37 (d, J=7.35 Hz, 1 H) 8.97 (d, J=8.82 Hz, 1 H) 9.98 (s, 1 H) 11.01 (s, 1 H) 14.37 (s, 1 H); MS (ESI+) m/z 580(M+H)+.

Sources & evidence

ORD record
ord-5217e9a556f242109cb9fb47a3bf23da
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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