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

HRID 2358594Notes

Reaction equation

HRID 2358594 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]([NH:20][CH2:21][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>>[CH2:21]([NH:20][C:18]1[CH:17]=[CH:16][C:15]([S:28][C:29]2[CH:30]=[CH:31][C:32]([OH:35])=[CH:33][CH:34]=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)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridineHCID 668084094-(2-Amino-4-benzylamino-phenylsulfanyl)-phenol

Product 1

HCID 248981864-[4-Benzylamino-2-(7-methyl-[1,8]naphthyridin-4-ylamino)-phenylsulfanyl]-phenol

Procedure

The product from Example 1d (57 mg, 0.319 mmol) was reacted with the product from Example 44c (102 mg, 0.319 mmol) for 72 h following the procedure from Example 1g giving the crude title compound which was purified by HPLC with TFA providing the trifluoroacetic acid salt (169 mg, 91%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.74 (s, 3H) 4.30 (s, 2H) 6.15 (d, J=6.99 Hz, 1H) 6.52 (d, J=8.46 Hz, 1H) 6.56-7.39 (m, 11H) 7.75 (d, J=8.46 Hz, 1H) 8.28 (d, J=7.36 Hz, 1H) 9.50 (br s, 1H) 10.85 (br s, 1H) 14.25 (br s, 1H); MS (ESI+) m/z 465 (M+H−TFA)+; (ESI−) m/z 463 (M−H−TFA)−.

Sources & evidence

ORD record
ord-decd51a8de8f4aa589f19363e149fff3
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

Loading…