5-Chloro-2-propyl-[1,8]naphthyridine → 4-[4-Chloro-2-(7-propyl-[1,8]naphthyridin-4-ylamino)-phenoxy]-N-(2-methoxy-ethyl)-benzamide

HRID 2358696Notes

Reaction equation

HRID 2358696 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:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:17]=1[O:18][C:19]1[CH:31]=[CH:30][C:22]([C:23]([NH:25][CH2:26][CH2:27][O:28][CH3:29])=[O:24])=[CH:21][CH:20]=1>>[Cl:36][C:34]1[CH:33]=[CH:32][C:17]([O:18][C:19]2[CH:31]=[CH:30][C:22]([C:23]([NH:25][CH2:26][CH2:27][O:28][CH3:29])=[O:24])=[CH:21][CH:20]=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:35]=1

Participants

3

Reactant 2

HCID 441401765-Chloro-2-propyl-[1,8]naphthyridineHCID 672493384-(2-amino-4-chlorophenoxy)-N-(2-methoxyethyl)benzamide

Product 1

HCID 684591584-[4-Chloro-2-(7-propyl-[1,8]naphthyridin-4-ylamino)-phenoxy]-N-(2-methoxy-ethyl)-benzamide

Procedure

The product from Example 2g (75 mg, 0.36 mmol) was reacted with the product from Example 126e (116 mg, 0.36 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 (101.7 mg, 46%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 0.95 (t, J=7.35 Hz, 3H) 1.70-1.90 (m, 2 H) 2.90-3.01 (m, 2 H) 3.24 (s, 3 H) 3.32-3.47 (m, 4 H) 6.73 (d, J=6.99 Hz, 1H) 6.98 (d, J=8.82 Hz, 2 H) 7.29 (d, J=8.82 Hz, 1 H) 7.61 (dd, J=8.82, 2.57 Hz, 1 H) 7.71-7.81 (m, 4H) 8.42 (t, J=4.78 Hz, 1 H) 8.53 (d, J=6.99 Hz, 1 H) 8.85 (d, J=8.82 Hz, 1 H) 10.92 (s, 1 H) 14.57 (s, 1 H); MS (ESI+) m/z 491 (M+H−TFA)+.

Sources & evidence

ORD record
ord-4a563850374e494cb047725d10cd3703
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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