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

HRID 2358695Notes

Reaction equation

HRID 2358695 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:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:17]=1[O:18][C:19]1[CH:30]=[CH:29][C:22]([C:23]([NH:25][CH2:26][CH2:27][CH3:28])=[O:24])=[CH:21][CH:20]=1>>[Cl:35][C:33]1[CH:32]=[CH:31][C:17]([O:18][C:19]2[CH:30]=[CH:29][C:22]([C:23]([NH:25][CH2:26][CH2:27][CH3:28])=[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:34]=1

Participants

3

Reactant 2

HCID 441401765-Chloro-2-propyl-[1,8]naphthyridineHCID 684596204-(2-amino-4-chlorophenoxy)-N-propylbenzamide

Product 1

HCID 684594634-[4-Chloro-2-(7-propyl-[1,8]naphthyridin-4-ylamino)-phenoxy]-N-propyl-benzamide

Procedure

The product from Example 2g (75 mg, 0.36 mmol) was reacted with the product from Example 127b (111 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 (25.8 mg, 12%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 0.86 (t, J=7.35 Hz, 3 H) 0.95 (t, J=7.35 Hz, 3 H) 1.37-1.56 (m, 2 H) 1.72-1.88 (m, 2 H) 2.96 (t, J=7.54 Hz, 2 H) 3.08-3.22 (m, 2 H) 6.72 (d, J=6.99 Hz, 1 H) 6.97 (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) 7.75 (d, J=8.82 Hz, 4 H) 8.34 (t, J=5.70 Hz, 1 H) 8.52 (d, J=6.99 Hz, 1 H) 8.85 (d, J=8.82 Hz, 1 H) 10.90 (s, 1 H) 14.55 (s, 1 H); MS (ESI+) m/z 475 (M+H−TFA)+.

Sources & evidence

ORD record
ord-9deed0bb499f4cd3bf4fb03f1cad0a9e
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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