5-Chloro-2-methyl-1,8-naphthyridine → N-{4-[4-(2-Methyl-allyloxy)-2-(7-methyl-[1,8]naphthyridin-4-ylamino)-phenylsulfanyl]-phenyl}-acetamide

HRID 2358841Notes

Reaction equation

HRID 2358841 reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:12])=[N:7]2.[NH2:13][C:14]1[CH:19]=[C:18]([O:20][CH2:21][C:22]([CH3:24])=[CH2:23])[CH:17]=[CH:16][C:15]=1[S:25][C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:33](=[O:35])[CH3:34])=[CH:28][CH:27]=1>C(O)C>[CH3:24][C:22](=[CH2:23])[CH2:21][O:20][C:18]1[CH:17]=[CH:16][C:15]([S:25][C:26]2[CH:31]=[CH:30][C:29]([NH:32][C:33](=[O:35])[CH3:34])=[CH:28][CH:27]=2)=[C:14]([NH:13][C:2]2[C:3]3[C:8](=[N:7][C:6]([CH3:12])=[CH:5][CH:4]=3)[N:9]=[CH:10][CH:11]=2)[CH:19]=1

Participants

4

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridineHCID 68460644N-{4-[2-Amino-4-(2-methyl-allyloxy)-phenylsulfanyl]-phenyl}-acetamide

Product 1

HCID 68460593N-{4-[4-(2-Methyl-allyloxy)-2-(7-methyl-[1,8]naphthyridin-4-ylamino)-phenylsulfanyl]-phenyl}-acetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Example 1d (30 mg, 0.17 mmol) was reacted in ethanol (1 mL) with the product from Example 234a (55 mg, 0.17 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 salt (12 mg, 25%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 1.76 (s, 3H) 2.02 (s, 3 H), 2.75 (s, 3 H), 4.52 (s, 2 H), 4.98 (s, 1 H), 5.05 (s, 1 H), 6.30 (d, J=7.35 Hz, 1 H), 7.04-7.19 (m, 4 H), 7.36 (s, 1 H), 7.41 (d, J=8.46 Hz, 2 H) 7.78 (d, J=8.82 Hz, 1 H), 8.37 (d, J=6.99 Hz, 1H), 8.94 (d, J=8.46 Hz, 1 H) 9.97 (s, 1 H), 10.99 (s, 1 H), 14.33 (s, 1 H); MS (ESI+) m/z 471(M+H)+.

Sources & evidence

ORD record
ord-a1eb8166ea0e4eec96b32c383f843048
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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