2-amino-4-fluoro-N-methylbenzamide → Diethyl (4-{[4-{[5-fluoro-2-(methylcarbamoyl)phenyl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate

HRID 511282Notes

Reaction equation

HRID 511282 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]=[C:39]([F:41])[CH:38]=[CH:37][C:32]=1[C:33]([NH:35][CH3:36])=[O:34]>>[F:41][C:39]1[CH:38]=[CH:37][C:32]([C:33](=[O:34])[NH:35][CH3:36])=[C:31]([NH:30][C:2]2[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]3[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]=3[O:28][CH3:29])[N:3]=2)[CH:40]=1

Participants

3

Reactant 2

HCID 569516612-amino-4-fluoro-N-methylbenzamideHCID 86654002Diethyl (4-{[4-chloro-5-(trifluoromethyl) pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate

Product 1

HCID 49821187Diethyl (4-{[4-{[5-fluoro-2-(methylcarbamoyl)phenyl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate

Procedure

The title compound was prepared using the procedure from Example 102 using diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate and 2-Amino-4-fluoro-N-methylbenzamide. 1H NMR (DMSO-d6, 400 MHz): δ=1.19 (t, J=7.07 Hz, 6H), 2.77 (d, J=4.55 Hz, 3 H), 3.16-3.24 (m, 2 H), 3.78 (s, 3 H), 3.92-4.01 (m, 4 H), 6.83 (d, J=7.83 Hz, 1 H), 6.93 (br. s., 1 H), 6.99 (s, 1 H), 7.53 (br. s., 1 H), 7.78 (t, J=7.33 Hz, 1 H), 8.25-8.48 (m, 2 H), 8.62-9.04 (m, 2 H), 11.86 (br. s., 1H). MS (ES+): m/z 586.18 [MH+] (TOF, polar).

Sources & evidence

ORD record
ord-751a8a7ebc5d4ea5b42166360f4df08b
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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