5-Chloro-2-methyl-1,8-naphthyridine → HCID 68457839, compound

HRID 2197745Notes

Reaction equation

HRID 2197745 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.[NH2:13][C:14]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:15]=1[S:24][C:25]1[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:34])[CH3:33])=[CH:27][CH:26]=1>>[CH3:12][C:6]1[N:7]=[C:8]2[C:3]([C:2]([NH:13][C:14]3[CH:19]=[C:18]([C:20]([F:22])([F:23])[F:21])[CH:17]=[CH:16][C:15]=3[S:24][C:25]3[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:34])[CH3:33])=[CH:27][CH:26]=3)=[CH:11][CH:10]=[N:9]2)=[CH:4][CH:5]=1

Participants

3

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridineHCID 68459602N-[4-(2-Amino-4-trifluoromethyl-phenylsulfanyl)-phenyl]-acetamide

Product 1

HCID 68457839HCID 68457839, compound

Procedure

The product from Example 1d (50 mg, 0.280 mmol) was reacted with the product from Example 35a (91 mg, 0.280 mmol) for 16 h following the procedure from Example 1g giving the crude title compound which was purified by HPLC with TFA providing the trifluoroacetic acid salt (21.5 mg, 20%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.07 (s, 3H), 2.78 (s, 3H), 6.43 (d, J=6.99 Hz, 1H), 7.09-7.15 (m, 1H), 7.44 (d, J=8.46 Hz, 2H), 7.68 (d, J=8.46 Hz, 2H), 7.78 (dd, J=8.64, 1.65 Hz, 1H), 7.84 (d, J=8.82 Hz, 1H), 7.92 (d, J=1.84 Hz, 1H), 8.52 (d, J=7.35 Hz, 1H), 9.00 (d, J=8.46 Hz, 1H), 10.19 (s, 1H), 11.12 (s, 1H); MS (ESI+) m/z 469 (M+H−TFA)+, (ESI−) m/z 467 (M−H−TFA)−.

Sources & evidence

ORD record
ord-5a9c5d0751ab43ecbe2bdb59da0bb959
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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