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

HRID 2197855Notes

Reaction equation

HRID 2197855 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:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:15]=1[O:16][C:17]1[CH:28]=[CH:27][C:20]([C:21]([N:23]([O:25][CH3:26])[CH3:24])=[O:22])=[CH:19][CH:18]=1>>[Cl:33][C:31]1[CH:30]=[CH:29][C:15]([O:16][C:17]2[CH:28]=[CH:27][C:20]([C:21]([N:23]([O:25][CH3:26])[CH3:24])=[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:32]=1

Participants

3

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridineHCID 866154954-(2-amino-4-chlorophenoxy)-N-methoxy-N-methylbenzamide

Product 1

HCID 866154964-(4-chloro-2-(7-methyl-1,8-naphthyridin-4-ylamino)phenoxy)-N-methoxy-N-methylbenzamide

Procedure

The product from Example 1d (111 mg, 0.62 mmol) was reacted with the product from Example 128b (192 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 (50.9 mg, 15%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.72 (s, 3H) 3.19 (s, 3H) 3.42 (s, 3H) 6.71 (d, J=6.99 Hz, 1H) 6.94 (d, J=8.82 Hz, 2H) 7.36 (d, J=8.82 Hz, 1H) 7.50 (d, J=8.82 Hz, 2H) 7.63 (dd, J=8.82, 2.57 Hz, 1H) 7.72 (d, J=8.82 Hz, 1H) 7.75 (d, J=2.57 Hz, 1H) 8.53 (d, J=6.99 Hz, 1H) 8.81 (d, J=8.46 Hz, 1H) 10.88 (s, 1H) 14.46 (s, 1H); MS (ESI+) m/z 449 (M+H−TFA)+.

Sources & evidence

ORD record
ord-caa6017c173049f8ba041341b7f685c2
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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