5-Chloro-2-methyl-1,8-naphthyridine → HCID 68459144, compound

HRID 2197971

Reaction equation

HRID 2197971 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][O:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:19]([NH2:29])[CH:18]=1)=[O:16]>>[CH3:13][O:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[C:19]([NH:29][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:18]=1)=[O:16]

Participants

3

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridineHCID 67497797Methyl 2-amino-[1,1'-biphenyl]-4-carboxylate

Product 1

HCID 68459144HCID 68459144, compound

Procedure

The product from Example 1d (0.0552 g, 0.309 mmol) was reacted with the product from Example 212c (0.070 g, 0.309 mmol) for 92 h following the procedure of Example 1g giving the crude title compound, which was purified by HPLC with AA. The resulting solid was triturated with 4N HCl in dioxane to generate the hydrochloride salt which was collected by vacuum filtration (0.0747 g, 55%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.72 (s, 3H) 3.91 (s, 3H) 6.27 (d, J=6.99 Hz, 1H) 7.30 (m, J=6.99 Hz, 3H) 7.52 (m, 2H) 7.74 (d, J=8.82 Hz, 1H) 7.79 (d, J=8.09 Hz, 1H) 8.09 (d, J=1.47 Hz, 1H) 8.16 (dd, J=7.91, 1.65 Hz, 1H) 8.30 (d, J=6.99 Hz, 1H) 9.15 (d, J=8.82 Hz, 1H) 11.54 (s, 1H); MS (ESI+) m/z 369.9 (M+H)+.

Sources & evidence

ORD record
ord-7dcbde1c82fc4f4b9a8c4ee29258f93a
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Linked notes

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