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

HRID 2358697Notes

Reaction equation

HRID 2358697 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]([N:25]([O:27][CH3:28])[CH3:26])=[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]([N:25]([O:27][CH3:28])[CH3:26])=[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 866154954-(2-amino-4-chlorophenoxy)-N-methoxy-N-methylbenzamide

Product 1

HCID 866154974-[4-Chloro-2-(7-propyl-[1,8]naphthyridin-4-ylamino)-phenoxy]-N-methoxy-N-methyl-benzamide

Procedure

The product from Example 2g (75 mg, 0.36 mmol) was reacted with the product from Example 128b (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 (76.3 mg, 36%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 0.88-1.03 (m, 3 H) 1.70-1.91 (m, 2 H) 2.88-3.00 (m, 2 H) 3.18 (s, 3 H) 3.42 (s, 3 H) 6.71 (d, J=7.35 Hz, 1 H) 6.94 (d, J=8.82 Hz, 2 H) 7.36 (d, J=8.82 Hz, 1 H) 7.50 (d, J=8.82 Hz, 2 H) 7.59-7.66 (m, 1 H) 7.71-7.79 (m, 2 H) 8.53 (d, J=6.99 Hz, 1 H) 8.84 (d, J=8.82 Hz, 1 H) 10.89 (s, 1 H) 14.54 (s, 1 H); MS (ESI+) m/z 477 (M+H−TFA)+.

Sources & evidence

ORD record
ord-c5383796f1b2471b8b393c1e99a60597
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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