5-Chloro-2-methyl-1,8-naphthyridine → HCID 24897972, compound

HRID 2358548Notes

Reaction equation

HRID 2358548 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:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1>>[CH3:20][C:18]1[CH:17]=[CH:16][C:15]([S:21][C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=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 668081234-(2-Amino-4-methyl-phenylsulfanyl)-phenol

Product 1

HCID 24897972HCID 24897972, compound

Procedure

The product from Example 1d (277 mg, 0.156 mmol) was reacted with the product from Example 4c (361 mg, 0.156 mmol) for 5 h by the procedure in Example 1g giving the title compound after purification of the crude product by HPLC with TFA as the trifluoroacetic acid salt (231 mg, 30%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.33 (s, 3H) 2.77 (s, 3H) 6.29 (d, J=6.99 Hz, 1H) 6.73 (d, J=8.82 Hz, 2H) 7.01 (d, J=7.72 Hz, 1H) 7.19 (d, J=8.46 Hz, 2H) 7.24 (s, 1H) 7.27 (s, 1H) 7.81 (d, J=8.82 Hz, 1H) 8.44 (d, J=6.99 Hz, 1H) 9.01 (d, J=8.82 Hz, 1H) 9.91 (s, 1H) 11.03 (s, 1H) 14.38 (br. s, 1H); MS (ESI+) m/z 374 (M+H)+.

Sources & evidence

ORD record
ord-0cef35bb692243569cf2c3627697ac64
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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