5-Chloro-2-methyl-1,8-naphthyridine → HCID 68459330, compound

HRID 2358650Notes

Reaction equation

HRID 2358650 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:28]=[C:27]([CH3:29])[CH:26]=[CH:25][C:15]=1[C:16]([NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:17]>>[CH3:29][C:27]1[CH:26]=[CH:25][C:15]([C:16]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:17])=[C:14]([NH:13][C:2]2[C:3]3[C:8](=[N:7][C:6]([CH3:12])=[CH:5][CH:4]=3)[N:9]=[CH:10][CH:11]=2)[CH:28]=1

Participants

3

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridineHCID 68456736HCID 68456736, compound

Product 1

HCID 68459330HCID 68459330, compound

Procedure

The product from Example 1d (150 mg, 0.84 mmol) was reacted with the product from Example 95c (190 mg, 0.84 mmol) for 6 h following the procedure from Example 1g giving the crude title compound which was purified by silica gel column chromatography eluting with 50:1 CH2Cl2/MeOH providing the title compound (210 mg, 68%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.40 (s, 3H), 2.68 (s, 3H), 6.62 (d, J=6.9 Hz, 1H), 6.98 (t, J=7.3 Hz, 1H), 7.19 (t, J=7.3 Hz, 2H), 7.36 (s, 1H), 7.38 (d, J=8.3 Hz, 1H), 7.52 (d, J=7.3 Hz, 2H), 7.67 (d, J=8.8 Hz, 1H), 7.78 (d, J=8.3 Hz, 1H), 8.40 (d, J=6.9 Hz, 1H), 8.94 (d, J=8.8 Hz, 1H); MS (ESI+) m/z 369 (M+H), ESI− m/z367 (M−H).

Sources & evidence

ORD record
ord-df96fd1de8e24618a528f70d848616ed
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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