5-Chloro-2-propyl-[1,8]naphthyridine → N-{3-Fluoro-4-[4-methyl-2-(7-propyl-[1,8]naphthyridin-4-ylamino)-phenylsulfanyl]-phenyl}-acetamide

HRID 2358583Notes

Reaction equation

HRID 2358583 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][C:25]=1[F:34]>>[F:34][C:25]1[CH:26]=[C:27]([NH:30][C:31](=[O:33])[CH3:32])[CH:28]=[CH:29][C:24]=1[S:23][C:17]1[CH:18]=[CH:19][C:20]([CH3:22])=[CH:21][C:16]=1[NH:15][C:2]1[C:3]2[C:8](=[N:7][C:6]([CH2:12][CH2:13][CH3:14])=[CH:5][CH:4]=2)[N:9]=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 441401765-Chloro-2-propyl-[1,8]naphthyridineHCID 68459226N-[4-(2-Amino-4-methyl-phenylsulfanyl)-3-fluoro-phenyl]-acetamide

Product 1

HCID 68460693N-{3-Fluoro-4-[4-methyl-2-(7-propyl-[1,8]naphthyridin-4-ylamino)-phenylsulfanyl]-phenyl}-acetamideYield 54.3%

Procedure

The product from Example 2g (100 mg, 0.48 mmol) was reacted with the product from Example 39e (140 mg, 0.48 mmol) for 22 h at 120° C. following the procedure from Example 1g giving the title compound as a solid (120 mg, 54%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 0.99 (t, J=7.3 Hz, 3H), 1.86 (sextet, J=7.3 Hz, 2H), 2.06 (s, 3H), 2.36 (s, 3H), 3.01 (t, J=7.3 Hz, 2H), 6.28 (d, J=6.9 Hz, 1H), 7.12-7.35 (m, 5H), 7.55 (dd, J=12.1, 2.2 Hz, 1H), 7.82 (d, J=8.8 Hz, 1H), 8.42 (d, J=6.9 Hz, 1H), 9.04 (d, J=8.8 Hz, 1H); MS (ESI+) m/z 461 (M+H)+, ESI− m/z 459 (M−H)−.

Sources & evidence

ORD record
ord-b1deb1b15512434fae62c25d66da4dcb
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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