4-Chloro-1,8-naphthyridine → 4-(2-(1,8-Naphthyridin-4-ylamino)-4-chlorophenoxy)-n-ethyl-n-methylbenzamide

HRID 2197864Notes

Reaction equation

HRID 2197864 reaction equation
Cl[C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[NH2:12][C:13]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:14]=1[O:15][C:16]1[CH:27]=[CH:26][C:19]([C:20]([N:22]([CH2:24][CH3:25])[CH3:23])=[O:21])=[CH:18][CH:17]=1>>[N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][N:7]=2)[C:2]([NH:12][C:13]2[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:14]=2[O:15][C:16]2[CH:27]=[CH:26][C:19]([C:20]([N:22]([CH2:24][CH3:25])[CH3:23])=[O:21])=[CH:18][CH:17]=2)=[CH:3][CH:4]=1

Participants

3

Reactant 2

HCID 124225244-Chloro-1,8-naphthyridineHCID 684562034-(2-amino-4-chlorophenoxy)-N-ethyl-N-methylbenzamide

Product 1

HCID 684590164-(2-(1,8-Naphthyridin-4-ylamino)-4-chlorophenoxy)-n-ethyl-n-methylbenzamide

Procedure

The product from Example 16c (100 mg, 0.61 mmol) was reacted with the product from Example 133b (185 mg, 0.61 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 (141 mg, 42%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 0.86-1.18 (m, 3H) 2.62-2.92 (m, 5H) 6.76 (d, J=7.35 Hz, 1H) 6.94 (d, J=8.82 Hz, 2H) 7.25 (d, J=8.09 Hz, 2H) 7.34 (d, J=8.82 Hz, 1H) 7.63 (dd, J=8.82, 2.57 Hz, 1H) 7.75 (d, J=2.57 Hz, 1H) 7.85 (dd, J=8.46, 4.41 Hz, 1H) 8.61 (d, J=6.99 Hz, 1H) 8.96 (dd, J=8.64, 1.29 Hz, 1H) 9.14 (dd, J=4.23, 1.29 Hz, 1H) 11.06 (s, 1H) 14.74 (s, 1H); MS (ESI+) m/z 433 (M+H−TFA)+.

Sources & evidence

ORD record
ord-fb1a682e301c4a47a0948883a1e65d22
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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