5-Chloro-2-methyl-1,8-naphthyridine → HCID 68461340, compound

HRID 2358617Notes

Reaction equation

HRID 2358617 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.[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([S:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][CH3:30])=[CH:23][CH:22]=2)=[C:16]([N+:31]([O-])=O)[CH:15]=1>>[CH3:12][C:6]1[N:7]=[C:8]2[C:3]([C:2]([NH:31][C:16]3[CH:15]=[C:14]([CH3:13])[CH:19]=[CH:18][C:17]=3[S:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][CH3:30])=[CH:23][CH:22]=3)=[CH:11][CH:10]=[N:9]2)=[CH:4][CH:5]=1

Participants

3

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridineHCID 68455815HCID 68455815, compound

Product 1

HCID 68461340HCID 68461340, compound

Procedure

The product from Example 1d (250 mg, 1.56 mmol) was reacted with the product from Example 55a (273 mg, 1.56 mmol) for 5 h following the procedure from Example 1g giving the crude title compound which was purified by HPLC with TFA providing the trifluoroacetic acid salt (187 mg, 23%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 0.97 (t, J=7.35 Hz, 3H) 1.62-1.79 (m, 2H) 2.34 (s, 3H) 2.76 (s, 3H) 3.86 (t, J=6.43 Hz, 2H) 6.27 (d, J=6.99 Hz, 1H) 6.84 (d, J=8.82 Hz, 2H) 7.11 (d, J=7.72 Hz, 1H) 7.24 (d, J=8.46 Hz, 2H) 7.29 (s, 1H) 7.80 (d, J=8.46 Hz, 1H) 8.42 (d, J=6.99 Hz, 1H) 8.99 (d, J=8.46 Hz, 1H) 11.01 (s, 1H) 14.39 (s, 1H); MS (ESI+) m/z 416 (M+H)+.

Sources & evidence

ORD record
ord-bd125b076578428c854b8d4153edef9d
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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