5-Chloro-2-methyl-1,8-naphthyridine → HCID 68461204, compound

HRID 2358726Notes

Reaction equation

HRID 2358726 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][C:25]([Br:28])=[CH:24][CH:23]=2)[CH:17]=[CH:16][C:15]=1[S:29][C:30]1[CH:35]=[CH:34][C:33]([NH:36][C:37](=[O:39])[CH3:38])=[CH:32][CH:31]=1>C(O)C>[Br:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][O:20][C:18]2[CH:17]=[CH:16][C:15]([S:29][C:30]3[CH:35]=[CH:34][C:33]([NH:36][C:37](=[O:39])[CH3:38])=[CH:32][CH:31]=3)=[C:14]([NH:13][C:2]3[C:3]4[C:8](=[N:7][C:6]([CH3:12])=[CH:5][CH:4]=4)[N:9]=[CH:10][CH:11]=3)[CH:19]=2)=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridineHCID 68458805HCID 68458805, compound

Product 1

HCID 68461204HCID 68461204, 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 158a (37 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 (26 mg, 42%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 0.97 (t, J=7.35 Hz, 3H) 1.67-1.92 (m, 2 H) 2.02 (s, 3 H) 2.99 (t, J=7.54 Hz, 2 H) 5.14 (s, 2 H) 6.30 (d, J=6.99 Hz, 1 H) 7.14 (d, J=8.46 Hz, 2 H) 7.16-7.26 (m, 2 H) 7.31-7.49 (m, 5 H) 7.53-7.66 (m, 2 H) 7.80 (d, J=8.46 Hz, 1 H) 8.37 (d, J=6.99 Hz, 1 H) 8.97 (d, J=8.82 Hz, 1 H) 9.97 (s, 1 H) 11.00 (s, 1 H) 14.37 (s, 1 H); MS (ESI+) m/z 615 (M+H)+.

Sources & evidence

ORD record
ord-47f310ee5d1143ffb3c5b1bb81b5a2e0
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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