5-Chloro-2-methyl-1,8-naphthyridine → HCID 68459184, compound

HRID 2358618Notes

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.[CH:13]([O:16][C:17]1[CH:22]=[CH:21][C:20]([S:23][C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:25]=2[NH2:31])=[CH:19][CH:18]=1)([CH3:15])[CH3:14]>>[CH:13]([O:16][C:17]1[CH:18]=[CH:19][C:20]([S:23][C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:25]=2[NH:31][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:21][CH:22]=1)([CH3:15])[CH3:14]

Participants

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridine

HCID 68457910HCID 68457910, compound

Product 1

HCID 68459184HCID 68459184, compound

Procedure

The product from Example 1d (250 mg, 1.56 mmol) was reacted with the product from Example 56a (427 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 (185 mg, 23%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 1.23 (d, J=6.25 Hz, 6H) 2.34 (s, 3H) 2.76 (s, 3H) 4.48-4.58 (m, 1H) 6.27 (d, J=6.99 Hz, 1H) 6.81 (d, J=8.82 Hz, 2H) 7.14 (d, J=8.09 Hz, 1H) 7.22 (d, J=8.82 Hz, 2H) 7.27 (s, 1H) 7.30 (s, 1H) 7.79 (d, J=8.82 Hz, 1H) 8.41 (d, J=6.99 Hz, 1H) 8.99 (d, J=8.46 Hz, 1H) 10.99 (s, 1H) 14.36 (s, 1H); MS (ESI+) m/z 416 (M+H)+.

Sources & evidence

ORD record: ord-05000e43589642fba5e744fa79c21b1d
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07763731B2

Reaction notes

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