5-Chloro-2-methyl-1,8-naphthyridine → HCID 68456156, compound

HRID 2197774Notes

Reaction equation

HRID 2197774 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]1[CH:16]=[C:17]([S:23][C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:25]=2[NH2:31])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]>>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([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:18]=[CH:19][C:20]=1[O:21][CH3:22]

Participants

3

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridineHCID 68457787HCID 68457787, compound

Product 1

HCID 68456156HCID 68456156, compound

Procedure

The product from Example 1d (277 mg, 1.56 mmol) was reacted with the product from Example 51b (430 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 (628 mg, 79%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.35 (s, 3H) 2.76 (s, 3H) 3.56 (s, 3H) 3.68 (s, 3H) 6.24 (d, J=6.99 Hz, 1H) 6.82 (m, 3H) 7.29 (m, 3H) 7.79 (d, J=8.46 Hz, 1H) 8.38 (d, J=6.99 Hz, 1H) 8.97 (d, J=8.46 Hz, 1H) 10.97 (s, 1H) 14.35 (s, 1H); MS (ESI+) m/z 418 (M+H)+.

Sources & evidence

ORD record
ord-048062c31ee34da1a2c0ed930c84399c
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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