5-Chloro-2-methyl-1,8-naphthyridine → 4-[2-(7-Methyl-[1,8]naphthyridin-4-ylamino)-4-phenoxymethyl-phenylsulfanyl]-phenol

HRID 2358821Notes

Reaction equation

HRID 2358821 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]([CH2:20][O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:17]=[CH:16][C:15]=1[S:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1>>[CH3:12][C:6]1[N:7]=[C:8]2[C:3]([C:2]([NH:13][C:14]3[CH:19]=[C:18]([CH2:20][O:21][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:17]=[CH:16][C:15]=3[S:28][C:29]3[CH:30]=[CH:31][C:32]([OH:35])=[CH:33][CH:34]=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 684602104-(2-Amino-4-phenoxymethyl-phenylsulfanyl)-phenol

Product 1

HCID 684617964-[2-(7-Methyl-[1,8]naphthyridin-4-ylamino)-4-phenoxymethyl-phenylsulfanyl]-phenol

Procedure

The product from Example 1d (0.037 g, 0.205 mmol) was reacted with the product from Example 221d (0.066 g, 0.205 mmol) for 16.5 hours 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 (0.041 g, 34%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.77 (s, 3 H) 5.13 (s, 2 H) 6.31 (d, J=6.99 Hz, 1 H) 6.79 (d, J=8.46 Hz, 2 H) 6.88-7.12 (m, 4 H) 7.20-7.36 (m, 4 H) 7.46-7.56 (m, 2 H) 7.81 (d, J=8.82 Hz, 1 H) 8.48 (d, J=6.99 Hz, 1 H) 9.02 (d, J=8.46 Hz, 1 H) 10.01 (s, 1H); MS (ESI+) m/z 466.3 (M+H)+; (ESI−) m/z 464.2 (M−H)−.

Sources & evidence

ORD record
ord-2046dfbcd85f4859964dd5de5ea64cd8
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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