2-Amino-3-fluoro-n-methylbenzamide → Diethyl (4-{[4-{[2-fluoro-6-(methylcarbamoyl)phenyl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate

HRID 511374Notes

Reaction equation

HRID 511374 reaction equation
FC1C=CC([NH:8][C:9]2[C:14]([C:15]([F:18])([F:17])[F:16])=[CH:13][N:12]=[C:11]([NH:19][C:20]3[CH:34]=[CH:33][C:23]([CH2:24][P:25](=[O:32])([O:29][CH2:30][CH3:31])[O:26][CH2:27][CH3:28])=[CH:22][C:21]=3[O:35][CH3:36])[N:10]=2)=C(C(=O)NC)C=1.ClC1C(C(F)(F)F)=CN=C(NC2C=CC(CP(=O)(OCC)OCC)=CC=2OC)N=1.N[C:71]1[C:80]([F:81])=[CH:79][CH:78]=[CH:77][C:72]=1[C:73]([NH:75][CH3:76])=[O:74]>>[F:81][C:80]1[CH:79]=[CH:78][CH:77]=[C:72]([C:73](=[O:74])[NH:75][CH3:76])[C:71]=1[NH:8][C:9]1[C:14]([C:15]([F:18])([F:17])[F:16])=[CH:13][N:12]=[C:11]([NH:19][C:20]2[CH:34]=[CH:33][C:23]([CH2:24][P:25](=[O:32])([O:29][CH2:30][CH3:31])[O:26][CH2:27][CH3:28])=[CH:22][C:21]=2[O:35][CH3:36])[N:10]=1

Participants

4

Reactant 3

HCID 272815042-Amino-3-fluoro-n-methylbenzamideHCID 49822431Diethyl (4-{[4-{[4-fluoro-2-(methylcarbamoyl)phenyl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonateHCID 86654002Diethyl (4-{[4-chloro-5-(trifluoromethyl) pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate

Product 1

HCID 58293038Diethyl (4-{[4-{[2-fluoro-6-(methylcarbamoyl)phenyl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate

Procedure

The title compound was prepared according to the procedure from Example 102 (Diethyl (4-{[4-{[4-fluoro-2-(methylcarbamoyl)-phenyl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate) using diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate and the commercially available 2-amino-3-fluoro-N-methylbenzamide. 1H NMR (CDCl3, 400 MHz): δ=1.26 (t, J=7.07 Hz, 6 H), 2.92 (d, J=4.80 Hz, 3 H), 3.03-3.12 (m, 2 H), 3.86 (s, 3 H), 3.95-4.07 (m, 4 H), 6.21 (q, J=4.97 Hz, 1 H), 6.57 (d, J=9.09 Hz, 1 H), 6.81 (t, J=1.89 Hz, 1 H), 7.28-7.36 (m, 3 H), 7.73 (br. s., 1 H), 7.85 (br. s., 1 H), 8.34 (s, 1 H), 8.89 (br. s., 1 H). MS (ES+): m/z 586.14 [MH+] (TOF, polar).

Sources & evidence

ORD record
ord-36eebb4ff1e84e67bef1aa462298287f
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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