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 1948007Notes

Reaction equation

HRID 1948007 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>>[CH2:20]([O:19][P:18]([CH2:17][C:16]1[CH:26]=[CH:27][C:13]([NH:12][C:4]2[N:3]=[C:2]([NH:30][C:31]3[CH:40]=[CH:39][CH:38]=[C:37]4[C:32]=3[C:33](=[O:42])[C:34]([CH3:41])=[CH:35][NH:36]4)[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=2)=[C:14]([O:28][CH3:29])[CH:15]=1)(=[O:25])[O:22][CH2:23][CH3:24])[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(1H)-one (Compound 203A). 1H NMR (DMSO-d6, 400 MHz): δ=1.20 (t, J=7.07 Hz, 6H), 1.98 (s, 3H), 3.24-3.31 (m, 2H), 3.75 (s, 3H), 3.94-4.04 (m, 4H), 6.90 (d, J=7.83 Hz, 1H), 7.04 (s, 1H), 7.08 (d, J=8.34 Hz, 1H), 7.34-7.44 (m, 1H), 7.50 (d, J=7.83 Hz, 1H), 7.94 (s, 1H), 8.37 (s, 1H), 8.48 (br. s., 1H), 8.91 (s, 1H), 11.86 (br. s., 1H), 14.41 (s, 1H). MS (ES+): m/z 592.14 [MH+] (TOF, polar).

Sources & evidence

ORD record
ord-e7a0ae949150434c94189218ce9acab0
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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