5-Chloro-2-methyl-1,8-naphthyridine → HCID 68459572, compound

HRID 2358843Notes

Reaction equation

HRID 2358843 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][CH2:22][CH3:23])[CH:17]=[CH:16][C:15]=1[S:24][C:25]1[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:34])[CH3:33])=[CH:27][CH:26]=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][CH2:22][CH3:23])[CH:17]=[CH:16][C:15]=3[S:24][C:25]3[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:34])[CH3:33])=[CH:27][CH:26]=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 68460915HCID 68460915, compound

Product 1

HCID 68459572HCID 68459572, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Example 1d (30 mg, 0.17 mmol) was reacted in ethanol (1 mL) with the product from Example 235a (55 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 (14 mg, 30%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 0.97 (t, J=7.35 Hz, 3 H) 1.59-1.83 (m, 2 H) 2.02 (s, 3 H) 2.75 (s, 3 H) 3.97 (t, J=6.43 Hz, 2 H) 6.31 (d, J=7.35 Hz, 1 H) 7.04-7.18 (m, 4 H) 7.25-7.45 (m, J=8.64, 3.86 Hz, 3 H) 7.77 (d, J=8.46 Hz, 1 H) 8.35 (d, J=7.35 Hz, 1 H) 8.94 (d, J=8.82 Hz, 1 H) 9.96 (s, 1 H) 10.99 (s, 1 H) 14.31 (s, 1 H); MS (ESI+) m/z 459 (M+H)+.

Sources & evidence

ORD record
ord-a297fc4d9cbf4aa49511ca74a3953b0e
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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