5-Chloro-2-methyl-1,8-naphthyridine → 4-(4-chloro-2-(7-methyl-1,8-naphthyridin-4-ylamino)phenoxy)-N,N-diethylbenzamide

HRID 2197858Notes

Reaction equation

HRID 2197858 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:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:15]=1[O:16][C:17]1[CH:29]=[CH:28][C:20]([C:21]([N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])=[O:22])=[CH:19][CH:18]=1>>[Cl:34][C:32]1[CH:31]=[CH:30][C:15]([O:16][C:17]2[CH:29]=[CH:28][C:20]([C:21]([N:23]([CH2:24][CH3:25])[CH2:26][CH3:27])=[O:22])=[CH:19][CH:18]=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:33]=1

Participants

3

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridineHCID 684606784-(2-amino-4-chlorophenoxy)-N,N-diethylbenzamide

Product 1

HCID 684569164-(4-chloro-2-(7-methyl-1,8-naphthyridin-4-ylamino)phenoxy)-N,N-diethylbenzamide

Procedure

The product from Example 1d (111 mg, 0.62 mmol) was reacted with the product from Example 129b (199 mg, 0.62 mmol) for 18 h following the procedure from Example 1g giving the crude title compound which was purified by HPLC with TFA providing the product as a trifluoroacetic acid (49.2 mg, 14%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 1.01 (s, 6H) 2.73 (s, 3H) 3.35 (s, 1H) 3.53-3.81 (m, 4H) 6.70 (d, J=7.35 Hz, 1H) 6.93 (d, J=8.46 Hz, 2H) 7.22 (d, J=8.82 Hz, 2H) 7.34 (d, J=8.82 Hz, 1H) 7.62 (dd, J=8.82, 2.57 Hz, 1H) 7.73 (d, J=6.25 Hz, 1H) 7.75 (s, 1H) 8.53 (d, J=6.99 Hz, 1H) 8.82 (d, J=8.82 Hz, 1H) 10.92 (s, 1H) 14.55 (s, 1H); MS (ESI+) m/z 461 (M+H−TFA)+.

Sources & evidence

ORD record
ord-0375956318fa4dd8be29f6aba0ac21eb
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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