N-[4-(2-Amino-4-methyl-phenylsulfanyl)-phenyl]-acetamide → N-{4-[4-Methyl-2-(7-propyl-[1,8]naphthyridin-4-ylamino)-phenylsulfanyl]-phenyl}-acetamide

HRID 2197734Notes

Reaction equation

HRID 2197734 reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:12][CH2:13][CH3:14])=[N:7]2.[NH2:15][C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:17]=1[S:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31](=[O:33])[CH3:32])=[CH:26][CH:25]=1>>[CH3:22][C:20]1[CH:19]=[CH:18][C:17]([S:23][C:24]2[CH:25]=[CH:26][C:27]([NH:30][C:31](=[O:33])[CH3:32])=[CH:28][CH:29]=2)=[C:16]([NH:15][C:2]2[C:3]3[C:8](=[N:7][C:6]([CH2:12][CH2:13][CH3:14])=[CH:5][CH:4]=3)[N:9]=[CH:10][CH:11]=2)[CH:21]=1

Participants

3

Reactant 2

HCID 43168935N-[4-(2-Amino-4-methyl-phenylsulfanyl)-phenyl]-acetamideHCID 441401765-Chloro-2-propyl-[1,8]naphthyridine

Product 1

HCID 68458165N-{4-[4-Methyl-2-(7-propyl-[1,8]naphthyridin-4-ylamino)-phenylsulfanyl]-phenyl}-acetamide

Procedure

The product from Example 2g (93 mg, 0.44 mmol) was reacted with the product from Example 18b (123 mg, 0.44 mmol) for 23 h following the procedure from Example 1g giving the title compound after purification of the crude product by HPLC with TFA as a trifluoroacetic acid salt solid (72 mg, 29%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 0.98 (t, J=7.35 Hz, 3H), 1.84 (dq, J=14.75, 7.46 Hz, 2H), 2.04 (s, 3H), 2.35 (s, 3H), 2.99 (t, J=7.35 Hz, 2H), 6.31 (d, J=6.99 Hz, 1H), 7.15 (d, J=8.09 Hz, 1H), 7.20-7.33 (m, 4H), 7.50 (d, J=8.46 Hz, 2H), 7.81 (d, J=8.46 Hz, 1H), 8.41 (d, J=6.99 Hz, 1H), 9.00 (d, J=8.46 Hz, 1H), 10.05 (s, 1H), 11.02 (s, 1H); MS (ESI+) m/z 443 (M+H)+; (ESI−) m/z 441 (M−H)−.

Sources & evidence

ORD record
ord-b21b0e837c484327ad922e428a15ae8b
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

Loading…