2-Amino-5-fluoro-N-methylbenzamide → ethyl[5-{[2-({4-[(diethoxyphosphoryl)methyl]-2-methoxyphenyl}amino)-5-(trifluoromethyl)pyrimidin-4-yl]amino}-3-methyl-4-oxoquinolin-1(4H)-yl]acetate

HRID 1948104Notes

Reaction equation

HRID 1948104 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:60])[C:46]([CH3:59])=[CH:47][N:48]2[CH2:53][C:54]([O:56][CH2:57][CH3:58])=[O:55]>>[CH2:57]([O:56][C:54](=[O:55])[CH2:53][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:34][CH2:35][CH3:36])([O:31][CH2:32][CH3:33])=[O:37])=[CH:27][C:26]=4[O:40][CH3:41])[N:15]=3)[CH:52]=[CH:51][CH:50]=2)[C:45](=[O:60])[C:46]([CH3:59])=[CH:47]1)[CH3:58]

Participants

4

Reactant 3

HCID 431325582-Amino-5-fluoro-N-methylbenzamideHCID 86654002Diethyl (4-{[4-chloro-5-(trifluoromethyl) pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonateHCID 86654058Ethyl (5-amino-3-methyl-4-oxoquinolin-1(4H)-yl)acetate

Product 1

HCID 58292890ethyl[5-{[2-({4-[(diethoxyphosphoryl)methyl]-2-methoxyphenyl}amino)-5-(trifluoromethyl)pyrimidin-4-yl]amino}-3-methyl-4-oxoquinolin-1(4H)-yl]acetate

Procedure

The title compound was prepared according to Compound 102A using diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate (50.0 mg, 0.110 mmol) and ethyl (5-amino-3-methyl-4-oxoquinolin-1(4H)-yl)acetate (Example 301A, 31.5 mg, 0.121 mmol). 1H NMR (CD3OD, 400 MHz): δ=1.24-1.32 (m, 9H), 2.12 (s, 3H), 3.29 (d, J=21.2 Hz, 2H), 4.05-4.16 (m, 6H), 4.84 (s, 2H), 6.91 (dt, J=2.8, 8.4 Hz, 1H), 7.04 (t, J=2.0 Hz, 1 H), 7.40 (d, J=8.8 Hz, 1H), 7.60 (t, J=8.4 Hz, 1H), 7.89 (s, 1H), 7.98 (d, J=8.0 Hz, 1H), 8.37 (s, 1H), 8.66 (d, J=7.6 Hz, 1H). MS (ES+): m/z 678.17 [MH+]. HPLC: tR=1.50 min (UPLC TOF, polar—3 min).

Workup

  1. customHPLC: tR=1.50 min (UPLC TOF, polar—3 min)

Sources & evidence

ORD record
ord-b88b02c9e6bd48de9f48f2c2746486ec
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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