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

HRID 2358685Notes

Reaction equation

HRID 2358685 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]([NH:23][CH2:24][CH2:25][O:26][CH3:27])=[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]([NH:23][CH2:24][CH2:25][O: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 672493384-(2-amino-4-chlorophenoxy)-N-(2-methoxyethyl)benzamide

Product 1

HCID 672509094-(4-chloro-2-(7-methyl-1,8-naphthyridin-4-ylamino)phenoxy)-N-(2-methoxyethyl)benzamide

Procedure

The product from Example 1d (111 mg, 0.62 mmol) was reacted with the product from Example 126e (200 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 (89.4 mg, 25%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 2.73 (s, 3 H) 3.25 (s, 3H) 3.32-3.50 (m, 4 H) 6.72 (d, J=6.99 Hz, 1 H) 6.97 (d, J=8.82 Hz, 2 H) 7.30 (d, J=8.82 Hz, 1 H) 7.61 (dd, J=8.82, 2.57 Hz, 1 H) 7.70-7.80 (m, 4H) 8.42 (t, J=5.15 Hz, 1 H) 8.53 (d, J=6.99 Hz, 1 H) 8.82 (d, J=8.82 Hz, 1 H) 10.90 (s, 1 H) 14.54 (s, 1 H); MS (ESI+) m/z 463 (M+H−TFA)+.

Sources & evidence

ORD record
ord-9e0c4e75f47d4a6ba19a7b97fb2823fb
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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