5-Chloro-2-propyl-[1,8]naphthyridine → HCID 68455937, compound

HRID 2358725Notes

Reaction equation

HRID 2358725 reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:12][CH2:13][CH3:14])=[N:7]2.[NH2:15][C:16]1[CH:21]=[C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Br:30])[CH:19]=[CH:18][C:17]=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>[Br:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[CH2:23][O:22][C:20]1[CH:19]=[CH:18][C:17]([S:31][C:32]2[CH:33]=[CH:34][C:35]([NH:38][C:39](=[O:41])[CH3:40])=[CH:36][CH:37]=2)=[C:16]([NH:15][C:2]2[C:3]3[C:8](=[N:7][C:6]([CH2:12][CH2:13][CH3:14])=[CH:5][CH:4]=3)[N:9]=[CH:10][CH:11]=2)[CH:21]=1

Participants

4

Reactant 2

HCID 441401765-Chloro-2-propyl-[1,8]naphthyridineHCID 68461548HCID 68461548, compound

Product 1

HCID 68455937HCID 68455937, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Example 2g (35 mg, 0.17 mmol) was reacted in ethanol (1 mL) with the product from Example 157a (75 mg, 0.17 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 (18 mg, 29%). 1H NMR (300 MHz, DMSO-d6), ppm: 0.97 (t, J=7.35 Hz, 3H), 1.72-1.92 (m, 2 H) 2.02 (s, 3 H), 2.99 (t, J=7.35 Hz, 2 H), 5.17 (s, 2 H), 6.33 (d, J=6.99 Hz, 1 H), 7.16 (d, J=8.46 Hz, 2 H), 7.18-7.28 (m, 2 H), 7.28-7.51 (m, 5 H), 7.60 (dd, J=7.54, 1.65 Hz, 1 H), 7.69 (d, J=6.99 Hz, 1 H), 7.81 (d, J=8.82 Hz, 1 H), 8.39 (d, J=6.99 Hz, 1 H), 8.97 (d, J=8.82 Hz, 1 H), 9.99 (s, 1 H), 11.02 (s, 1 H), 14.37 (s, 1 H): MS (ESI+) m/z 613M+H)+.

Sources & evidence

ORD record
ord-7d73ec39aab84ebeba44e6abeec6a290
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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