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

HRID 2198002Notes

Reaction equation

HRID 2198002 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]#[N:23])[CH:17]=[CH:16][C:15]=1[S:24][C:25]1[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:34])[CH3:33])=[CH:27][CH:26]=1>C(O)C>[C:22]([CH2:21][O:20][C:18]1[CH:17]=[CH:16][C:15]([S:24][C:25]2[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:34])[CH3:33])=[CH:27][CH:26]=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)#[N:23]

Participants

4

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridineHCID 67249992N-[4-(2-Amino-4-cyanomethoxy-phenylsulfanyl)-phenyl]-acetamide

Product 1

HCID 67249372N-{4-[4-Cyanomethoxy-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 232c (53 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 (9 mg, 19%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.03 (s, 3H) 2.76 (s, 3H), 5.23 (s, 2H), 6.32 (d, J=6.99 Hz, 1H), 7.18 (d, J=8.46 Hz, 2H) 7.23 (dd, J=8.82, 2.57 Hz, 1H), 7.31 (d, J=2.57 Hz, 1H), 7.38 (d, J=8.82 Hz, 1H) 7.45 (d, J=8.82 Hz, 2H), 7.80 (d, J=8.46 Hz, 1H), 8.41 (d, J=6.99 Hz, 1H) 8.96 (d, J=8.46 Hz, 1H), 10.01 (s, 1H), 11.04 (s, 1H), 14.42 (s, 1H); MS (ESI+) m/z 456 (M+H)+.

Sources & evidence

ORD record
ord-eb3892427c3f45b48e571cef3a8676ca
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

Loading…