5-Chloro-2-methyl-1,8-naphthyridine → N-{4-[4-(3-Methyl-benzyloxy)-2-(7-methyl-[1,8]naphthyridin-4-ylamino)-phenylsulfanyl]-phenyl}-acetamide

HRID 2197834Notes

Reaction equation

HRID 2197834 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]2[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[CH:23]=2)[CH:17]=[CH:16][C:15]=1[S:29][C:30]1[CH:35]=[CH:34][C:33]([NH:36][C:37](=[O:39])[CH3:38])=[CH:32][CH:31]=1>C(O)C>[CH3:28][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=1)[CH2:21][O:20][C:18]1[CH:17]=[CH:16][C:15]([S:29][C:30]2[CH:35]=[CH:34][C:33]([NH:36][C:37](=[O:39])[CH3:38])=[CH:32][CH:31]=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 67250731N-{4-[2-Amino-4-(3-methyl-benzyloxy)-phenylsulfanyl]-phenyl}-acetamide

Product 1

HCID 67250116N-{4-[4-(3-Methyl-benzyloxy)-2-(7-methyl-[1,8]naphthyridin-4-ylamino)-phenylsulfanyl]-phenyl}-acetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Example 1d (18 mg, 0.085 mmol) was reacted in ethanol (1 mL) with the product from Example 120a (32 mg, 0.085 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 (14 mg, 26%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 0.97 (t, J=7.35 Hz, 3H) 1.62-1.93 (m, 2H) 2.02 (s, 3H) 2.31 (s, 3H) 2.99 (t, J=7.35 Hz, 2H) 5.11 (s, 2H) 6.30 (d, J=6.99 Hz, 1H) 6.97-7.33 (m, 8H) 7.34-7.50 (m, 3H) 7.80 (d, J=8.82 Hz, 1H) 8.36 (d, J=6.99 Hz, 1H) 8.97 (d, J=8.82 Hz, 1H) 9.97 (s, 1H) 11.01 (s, 1H) 14.36 (s, 1H); MS (ESI+) m/z 549 (M+H)+.

Sources & evidence

ORD record
ord-ef71f5f23cc34d40adeb9233e906fe86
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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