5-Chloro-2-methyl-1,8-naphthyridine → HCID 68461335, compound

HRID 2358601Notes

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][C:14]1[CH:15]=[CH:16][C:17]([S:21][C:22]2[CH:23]=[C:24]([CH3:28])[CH:25]=[CH:26][CH:27]=2)=[C:18]([NH2:20])[CH:19]=1>>[CH3:12][C:6]1[N:7]=[C:8]2[C:3]([C:2]([NH:20][C:18]3[CH:19]=[C:14]([CH3:13])[CH:15]=[CH:16][C:17]=3[S:21][C:22]3[CH:23]=[C:24]([CH3:28])[CH:25]=[CH:26][CH:27]=3)=[CH:11][CH:10]=[N:9]2)=[CH:4][CH:5]=1

Participants

Reactant 2

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

HCID 61244331HCID 61244331, compound

Product 1

HCID 68461335HCID 68461335, compound

Procedure

The product from Example 1d (267 mg, 1.56 mmol) was reacted with the product from Example 48b (358 mg, 1.56 mmol) for 48 h following the procedure from Example 1g giving the crude title compound which was purified by HPLC with TFA providing the trifluoroacetic acid salt (116 mg, 15%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.10 (s, 3H) 2.38 (s, 3H) 2.76 (s, 3H) 6.27 (d, J=7.35 Hz, 1H) 7.00 (m, 3H) 7.40 (m, 3H) 7.78 (d, J=8.82 Hz, 1H) 8.37 (d, J=6.99 Hz, 1H) 8.92 (d, J=8.82 Hz, 1H) 11.08 (br. s., 1H) 14.45 (br. s., 1H); MS (ESI+) m/z 372 (M+H)+.

Sources & evidence

ORD record: ord-f978d2cb779f477fa1c2cd4f4d6cd0ef
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07763731B2

Reaction notes

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