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 511435Notes

Reaction equation

HRID 511435 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][CH:14]=2)[N:3]=1.[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>>[CH3:39][C:32]1[C:31](=[O:40])[C:30]2[C:35](=[CH:36][CH:37]=[CH:38][C:29]=2[NH:28][C:2]2[C:7]([C:8]([F:10])([F:11])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]3[CH:14]=[CH:15][C:16]([CH2:17][P:18](=[O:25])([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21])=[CH:26][CH:27]=3)[N:3]=2)[NH:34][CH:33]=1

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, 6 H), 2.00 (s, 3 H), 3.15-3.25 (m, 2 H), 3.96 (qd, J=7.37, 7.20 Hz, 4 H), 7.16 (d, J=7.83 Hz, 1 H), 7.24 (dd, J=8.59, 2.27 Hz, 2 H), 7.51 (t, J=7.96 Hz, 1 H), 7.61 (d, J=6.82 Hz, 2 H), 7.97 (d, J=5.81 Hz, 1 H), 8.45 (s, 1 H), 8.71 (br. s., 1 H), 9.84 (s, 1 H), 12.01 (d, J=6.06 Hz, 1 H), 14.42 (br. s., 1 H). MS (ES+): m/z 562.13 [MH+] (TOF, polar).

Sources & evidence

ORD record
ord-1f92978446b146559ea88a81ad8e19f7
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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