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

HRID 1948005Notes

Reaction equation

HRID 1948005 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[N:22]=[C:21](Cl)[C:20]([C:24]([F:27])([F:26])[F:25])=[CH:19][N:18]=2)=[CH:12][CH:11]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[NH2:28][C:29]1[CH:38]=[CH:37][CH:36]=[C:35]2[C:30]=1[C:31](=[O:40])[C:32]([CH3:39])=[CH:33][NH:34]2>>[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[N:22]=[C:21]([NH:28][C:29]3[CH:38]=[CH:37][CH:36]=[C:35]4[C:30]=3[C:31](=[O:40])[C:32]([CH3:39])=[CH:33][NH:34]4)[C:20]([C:24]([F:27])([F:26])[F:25])=[CH:19][N:18]=2)=[CH:12][CH:11]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

3

Reactant 2

HCID 672540655-amino-3-methylquinolin-4(1H)-one2×HCID 86654003Diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate

Product 1

HCID 58293056Diethyl [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}benzyl)phosphonate and 5-amino-3-methylquinolin-4(1H)-one (Compound 203A). 1H NMR (DMSO-d6, 400 MHz): δ=1.18 (t, J=7.07 Hz, 6H), 2.00 (s, 3H), 3.15-3.25 (m, 2H), 3.96 (qd, J=7.37, 7.20 Hz, 4H), 7.16 (d, J=7.83 Hz, 1H), 7.24 (dd, J=8.59, 2.27 Hz, 2H), 7.51 (t, J=7.96 Hz, 1H), 7.61 (d, J=6.82 Hz, 2H), 7.97 (d, J=5.81 Hz, 1H), 8.45 (s, 1H), 8.71 (br. s., 1H), 9.84 (s, 1H), 12.01 (d, J=6.06 Hz, 1H), 14.42 (br. s., 1H). MS (ES+): m/z 562.13 [MH+] (TOF, polar).

Sources & evidence

ORD record
ord-beaeeb8cbf5443019130c805cf463dc0
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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