5-Chloro-2-methyl-1,8-naphthyridine → N,N-Dimethyl-3-[4-methyl-2-(7-methyl-[1,8]naphthyridin-4-ylamino)-phenylsulfanyl]-benzamide

HRID 2358640Notes

Reaction equation

HRID 2358640 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[S:9][C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=1)[C:13]([N:15]([CH3:17])[CH3:16])=[O:14].Cl[C:22]1[CH:31]=[CH:30][N:29]=[C:28]2[C:23]=1[CH:24]=[CH:25][C:26]([CH3:32])=[N:27]2>>[CH3:16][N:15]([CH3:17])[C:13](=[O:14])[C:12]1[CH:18]=[CH:19][CH:20]=[C:10]([S:9][C:3]2[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=2[NH:1][C:22]2[C:23]3[C:28](=[N:27][C:26]([CH3:32])=[CH:25][CH:24]=3)[N:29]=[CH:30][CH:31]=2)[CH:11]=1

Participants

3

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridineHCID 684608313-(2-Amino-4-methyl-phenylsulfanyl)-N,N-dimethyl-benzamide

Product 1

HCID 68456354N,N-Dimethyl-3-[4-methyl-2-(7-methyl-[1,8]naphthyridin-4-ylamino)-phenylsulfanyl]-benzamide

Procedure

The product from Example 88b (0.175 g, 0.610 mmol) was reacted with the product from Example 1d (0.109 g, 0.61 mmol) for 24 h following the procedure from Example 1g giving the crude title compound which was purified by HPLC with TFA providing the product as a trifluoroacetic acid salt (0.1552 g, 45%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.40 (s, 3H) 2.75 (s, 6H) 2.92 (s, 3H) 6.34 (d, J=6.99 Hz, 1H) 7.11-7.53 (m, 7H) 7.76 (d, J=8.82 Hz, 1H) 8.39 (d, J=6.99 Hz, 1H) 8.94 (d, J=8.82 Hz, 1H); MS (ESI+) m/z 429.0 (M+H)+; (ESI−) m/z 427.0 (M−H)−

Sources & evidence

ORD record
ord-d217194cec3d418aac12faaee2e3c78c
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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