5-Chloro-2-propyl-[1,8]naphthyridine → [3-(4-Bromo-benzyloxy)-5-chloro-phenyl]-(7-propyl-[1,8]naphthyridin-4-yl)-amine

HRID 2197953Notes

Reaction equation

HRID 2197953 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.[Br:15][C:16]1[CH:31]=[CH:30][C:19]([CH2:20][O:21][C:22]2[CH:23]=[C:24]([NH2:29])[CH:25]=[C:26]([Cl:28])[CH:27]=2)=[CH:18][CH:17]=1>>[Br:15][C:16]1[CH:31]=[CH:30][C:19]([CH2:20][O:21][C:22]2[CH:23]=[C:24]([NH:29][C:2]3[C:3]4[C:8](=[N:7][C:6]([CH2:12][CH2:13][CH3:14])=[CH:5][CH:4]=4)[N:9]=[CH:10][CH:11]=3)[CH:25]=[C:26]([Cl:28])[CH:27]=2)=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 441401765-Chloro-2-propyl-[1,8]naphthyridineHCID 684611983-(4-Bromo-benzyloxy)-5-chloro-phenylamine

Product 1

HCID 68460460[3-(4-Bromo-benzyloxy)-5-chloro-phenyl]-(7-propyl-[1,8]naphthyridin-4-yl)-amine

Procedure

The product from Example 2g (100 mg, 0.39 mmol) was reacted with the product from Example 196b (120 mg, 0.39 mmol) for 22 h following the procedure from Example 1g giving the crude title compound which was purified by trituration with EtOAc providing the title compound (1990 mg, 100%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 0.96 (t, J=7.4 Hz, 3H), 1.83 (sextet, J=7.4 Hz, 2H), 2.97 (t, J=7.4 Hz, 2H), 5.18 (s, 2H), 6.91 (d, J=6.7 Hz, 1H), 7.05-7.17 (m, 3H), 7.43 (d, J=8.4 Hz, 2H), 7.63 (d, J=8.4 Hz, 2H), 7.73 (d, J=8.5 Hz, 1H), 8.51 (d, J=6.7 Hz, 1H), 9.05 (d, J=8.5 Hz, 1H); MS (ESI+) m/z 482, 484, 486 (M+H)+, (ESI−) m/z 480, 482, 484 (M−H)−.

Sources & evidence

ORD record
ord-0a8a4cb02ed4474fba7a1053d0fae150
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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