5-Chloro-2-propyl-[1,8]naphthyridine → 3-[4-Chloro-2-(7-propyl-[1,8]naphthyridin-4-ylamino)-phenoxy]-N,N-dimethyl-benzamide

HRID 2358744Notes

Reaction equation

HRID 2358744 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:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:17]=1[O:18][C:19]1[CH:20]=[C:21]([CH:27]=[CH:28][CH:29]=1)[C:22]([N:24]([CH3:26])[CH3:25])=[O:23]>C(O)C>[Cl:34][C:32]1[CH:31]=[CH:30][C:17]([O:18][C:19]2[CH:20]=[C:21]([CH:27]=[CH:28][CH:29]=2)[C:22]([N:24]([CH3:26])[CH3:25])=[O:23])=[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:33]=1

Participants

4

Reactant 2

HCID 441401765-Chloro-2-propyl-[1,8]naphthyridineHCID 684592683-(2-Amino-4-chloro-phenoxy)-N,N-dimethyl-benzamide

Product 1

HCID 684578753-[4-Chloro-2-(7-propyl-[1,8]naphthyridin-4-ylamino)-phenoxy]-N,N-dimethyl-benzamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Example 2g (177 mg, 0.86 mmol) was reacted with the product from Example 168d (249 mg, 0.86 mmol) in ethanol (5 mL) at 85° C. in a sealed tube for 18 h giving the crude title compound which was purified by HPLC with TFA providing the product as the trifluoroacetic acid (100 mg, 20.2%). 1H NMR (500 MHz, DMSO-D6) δ ppm: 8.86 (d, J=8.79 Hz, 1H) 8.52 (d, J=6.84 Hz, 1 H) 7.74 (d, 1 H) 7.72 (d, 1H) 7.60 (dd, J=8.79, 2.93 Hz, 1 H) 7.28-7.33 (m, 1 H) 7.27 (d, 2H) 7.06 (d, J=7.81 Hz, 1 H) 6.99 (dd, J=8.06, 2.69 Hz, 1 H) 6.71 (d, J=6.84 Hz, 1 H) 2.96 (t, 2 H) 2.91 (s, 3 H) 2.70 (s, 3 H) 1.79-1.86 (m, 2 H) 0.96 (t, J=7.49 Hz, 3 H); MS (ESI+) m/z 461 (M+H)+.

Sources & evidence

ORD record
ord-0c15cbdd6d1d4219bcc9b4c9070ab555
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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