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

HRID 2197776Notes

Reaction equation

HRID 2197776 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]([CH3:20])[CH:17]=[CH:16][C:15]=1[S:21][C:22]1[CH:23]=[C:24]([OH:28])[CH:25]=[CH:26][CH:27]=1>>[CH3:20][C:18]1[CH:17]=[CH:16][C:15]([S:21][C:22]2[CH:23]=[C:24]([OH:28])[CH:25]=[CH:26][CH:27]=2)=[C:14]([NH:13][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:19]=1

Participants

3

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridineHCID 574699063-(2-Amino-4-methyl-phenylsulfanyl)-phenol

Product 1

HCID 248981873-[4-Methyl-2-(7-methyl-[1,8]naphthyridin-4-ylamino)-phenylsulfanyl]-phenol

Procedure

The product from Example 1d (277 mg, 1.56 mmol) was reacted with the product from Example 52b (245 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 (399 mg, 52%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.38 (s, 3H) 2.75 (s, 3H) 6.30 (d, J=6.99 Hz, 1H) 6.53-6.58 (m, 2H) 6.61 (d, J=8.09 Hz, 1H) 6.90-7.08 (m, 1H) 7.27-7.47 (m, 3H) 7.77 (d, J=8.46 Hz, 1H) 8.39 (d, J=6.99 Hz, 1H) 8.94 (d, J=8.82 Hz, 1H) 9.58 (s, 1H) 10.96 (s, 1H) 14.34 (s, 1H); MS (ESI+) m/z 374 (M+H)+.

Sources & evidence

ORD record
ord-89ff92050cee4bf1be8e2d47fb19745d
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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