5-amino-3-methylquinolin-4(1H)-one → Diethyl[3-methoxy-4-({4-[(3-methyl-4-oxo-1,4-dihydroquinolin-5-yl)amino]-5-(trifluoromethyl)pyrimidin-2-yl}amino)benzyl]phosphonate

HRID 511437Notes

Reaction equation

HRID 511437 reaction equation
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:27]=[CH:26][C:16]([CH2:17][P:18](=[O:25])([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21])=[CH:15][C:14]=2[O:28][CH3:29])[N:3]=1.[NH2:30][C:31]1[CH:40]=[CH:39][CH:38]=[C:37]2[C:32]=1[C:33](=[O:42])[C:34]([CH3:41])=[CH:35][NH:36]2>>[CH3:29][O:28][C:14]1[CH:15]=[C:16]([CH:26]=[CH:27][C:13]=1[NH:12][C:4]1[N:3]=[C:2]([NH:30][C:31]2[CH:40]=[CH:39][CH:38]=[C:37]3[C:32]=2[C:33](=[O:42])[C:34]([CH3:41])=[CH:35][NH:36]3)[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=1)[CH2:17][P:18](=[O:25])([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21]

Participants

3

Reactant 2

HCID 672540655-amino-3-methylquinolin-4(1H)-one2×HCID 86654002Diethyl (4-{[4-chloro-5-(trifluoromethyl) pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate

Product 1

HCID 58292922Diethyl[3-methoxy-4-({4-[(3-methyl-4-oxo-1,4-dihydroquinolin-5-yl)amino]-5-(trifluoromethyl)pyrimidin-2-yl}amino)benzyl]phosphonate

Procedure

The title compound was prepared according to the procedure for Example 102 using diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate and 5-amino-3-methylquinolin-4(1 H)-one (Compound 203A). 1H NMR (DMSO-d6, 400 MHz): δ=1.20 (t, J=7.07 Hz, 6 H), 1.98 (s, 3 H), 3.24-3.31 (m, 2 H), 3.75 (s, 3 H), 3.94-4.04 (m, 4 H), 6.90 (d, J=7.83 Hz, 1 H), 7.04 (s, 1 H), 7.08 (d, J=8.34 Hz, 1 H), 7.34-7.44 (m, 1 H), 7.50 (d, J=7.83 Hz, 1 H), 7.94 (s, 1 H), 8.37 (s, 1 H), 8.48 (br. s., 1 H), 8.91 (s, 1 H), 11.86 (br. s., 1 H), 14.41 (s, 1 H). MS (ES+): tniz 592.14 [MH+] (TOF, polar).

Sources & evidence

ORD record
ord-7490c67c8c5845149a7dad7e75f64eb6
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

Loading…