5-Chloro-2-methyl-1,8-naphthyridine → HCID 68458146, compound

HRID 2358616Notes

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.[CH2:13]([O:15][C:16]1[CH:21]=[CH:20][C:19]([S:22][C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][C:24]=2[N+:30]([O-])=O)=[CH:18][CH:17]=1)[CH3:14]>>[CH2:13]([O:15][C:16]1[CH:17]=[CH:18][C:19]([S:22][C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][C:24]=2[NH:30][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:20][CH:21]=1)[CH3:14]

Participants

Reactant 2

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

HCID 68460523HCID 68460523, compound

Product 1

HCID 68458146HCID 68458146, compound

Procedure

The product from Example 1d (250 mg, 1.56 mmol) was reacted with the product from Example 54a (259 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 (241 mg, 30%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 1.31 (t, J=6.99 Hz, 3H) 2.34 (s, 3H) 2.76 (s, 3H) 3.97 (q, J=6.99 Hz, 2H) 6.26 (d, J=7.35 Hz, 1H) 6.83 (d, J=8.82 Hz, 2H) 7.11 (d, J=7.72 Hz, 1H) 7.24 (d, J=8.82 Hz, 2H) 7.27 (s, 1H) 7.30 (s, 1H) 7.80 (d, J=8.82 Hz, 1H) 8.41 (d, J=6.99 Hz, 1H) 8.99 (d, J=8.82 Hz, 1H) 11.01 (s, 1H) 14.38 (s, 1H); MS (ESI+) m/z 402 (M+H)+.

Sources & evidence

ORD record: ord-f810009a3a3e4afcac7b7af976d60740
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07763731B2

Reaction notes

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