2-Amino-5-fluoro-N-methylbenzamide → Diethyl [4-({4-[(1,3-dimethyl-4-oxo-1,4-dihydroquinolin-5-yl)amino]-5-(trifluoromethyl)pyrimidin-2-yl}amino)-3-methoxybenzyl]phosphonate

HRID 511534Notes

Reaction equation

HRID 511534 reaction equation
NC1C=CC(F)=CC=1C(NC)=O.Cl[C:14]1[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][N:17]=[C:16]([NH:24][C:25]2[CH:39]=[CH:38][C:28]([CH2:29][P:30](=[O:37])([O:34][CH2:35][CH3:36])[O:31][CH2:32][CH3:33])=[CH:27][C:26]=2[O:40][CH3:41])[N:15]=1.[NH2:42][C:43]1[CH:52]=[CH:51][CH:50]=[C:49]2[C:44]=1[C:45](=[O:55])[C:46]([CH3:54])=[CH:47][N:48]2[CH3:53]>>[CH3:53][N:48]1[C:49]2[C:44](=[C:43]([NH:42][C:14]3[C:19]([C:20]([F:21])([F:23])[F:22])=[CH:18][N:17]=[C:16]([NH:24][C:25]4[CH:39]=[CH:38][C:28]([CH2:29][P:30](=[O:37])([O:31][CH2:32][CH3:33])[O:34][CH2:35][CH3:36])=[CH:27][C:26]=4[O:40][CH3:41])[N:15]=3)[CH:52]=[CH:51][CH:50]=2)[C:45](=[O:55])[C:46]([CH3:54])=[CH:47]1

Participants

4

Reactant 3

HCID 431325582-Amino-5-fluoro-N-methylbenzamideHCID 672550595-amino-1,3-dimethylquinolin-4(1H)-one2×HCID 86654002Diethyl (4-{[4-chloro-5-(trifluoromethyl) pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate

Product 1

HCID 58293039Diethyl [4-({4-[(1,3-dimethyl-4-oxo-1,4-dihydroquinolin-5-yl)amino]-5-(trifluoromethyl)pyrimidin-2-yl}amino)-3-methoxybenzyl]phosphonate

Procedure

The title compound was prepared according to Compound 102A using diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate (99.5 mg, 0.219 mmol) and 5-amino-1,3-dimethylquinolin-4(1H)-one (Compound 299A, 49.2 mg, 0.261 mmol). 1H NMR (400 MHz, DMSO-d6) δ ppm 14.66 (s, 1H), 8.88 (s, 1H), 8.60 (br s, 1H), 8.38 (s, 1H), 8.07 (s, 1H), 7.43-7.63 (m, 2H), 7.18 (d, J=8.6 Hz, 1H), 7.05 (s, 1H), 6.90 (d, J=7.8 Hz, 1H), 3.95-4.05 (m, 4H), 3.80 (s, 3H), 3.76 (s, 3H), 3.28 (d, J=21.5 Hz, 2H), 1.98 (s, 3H), 1.20 (t, J=6.9 Hz, 6H). MS (ES+): m/z 606.16 (60) [MH+]. HPLC: tR=1.46 min (TOF, polar—3 min).

Workup

  1. customHPLC: tR=1.46 min (TOF, polar—3 min)

Sources & evidence

ORD record
ord-f3afddfcaa434058ac322ac3476fd952
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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