Ethyl hydrogen (4-{[4-{[6-bromo-2-(methylcarbamoyl)pyridin-3-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate → Ethyl hydrogen (4-{[4-{[6-bromo-2-(methylcarbamoyl)pyridin-3-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-2-chloro-5-methoxybenzyl)phosphonate

HRID 2279870Notes

Reaction equation

HRID 2279870 reaction equation
BrC1N=C(C(=O)NC)C(NC2C(C(F)(F)F)=CN=C(NC3C=CC(CP(=O)(O)OCC)=CC=3OC)N=2)=CC=1.[Br:39][C:40]1[N:45]=[C:44]([C:46](=[O:49])[NH:47][CH3:48])[C:43]([NH:50][C:51]2[C:56]([C:57]([F:60])([F:59])[F:58])=[CH:55][N:54]=[C:53]([NH:61][C:62]3[C:76]([O:77][CH3:78])=[CH:75][C:65]([CH2:66][P:67](=[O:74])([O:71]CC)[O:68][CH2:69][CH3:70])=[C:64]([Cl:79])[CH:63]=3)[N:52]=2)=[CH:42][CH:41]=1>>[Br:39][C:40]1[N:45]=[C:44]([C:46](=[O:49])[NH:47][CH3:48])[C:43]([NH:50][C:51]2[C:56]([C:57]([F:60])([F:59])[F:58])=[CH:55][N:54]=[C:53]([NH:61][C:62]3[C:76]([O:77][CH3:78])=[CH:75][C:65]([CH2:66][P:67](=[O:71])([OH:74])[O:68][CH2:69][CH3:70])=[C:64]([Cl:79])[CH:63]=3)[N:52]=2)=[CH:42][CH:41]=1

Participants

3

Reactant 2

HCID 86697762Ethyl hydrogen (4-{[4-{[6-bromo-2-(methylcarbamoyl)pyridin-3-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonateHCID 86697807Diethyl (4-{[4-{[6-bromo-2-(methylcarbamoyl)pyridin-3-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-2-chloro-5-methoxybenzyl)phosphonate2×

Product 1

HCID 86697806Ethyl hydrogen (4-{[4-{[6-bromo-2-(methylcarbamoyl)pyridin-3-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-2-chloro-5-methoxybenzyl)phosphonate

Procedure

Prepared analogously to Compound 38C replacing Compound 38B with diethyl (4-{[4-{[6-bromo-2-(methylcarbamoyl)pyridin-3-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-2-chloro-5-methoxybenzyl)phosphonate (Compound 56C). 1H NMR (400 MHz, DMSO-d6) δ=12.39 (br. s., 1H), 9.18 (br. s., 1H), 8.91-8.99 (m, 1H), 8.49 (s, 1H), 7.71 (d, J=9.1 Hz, 1H), 7.64 (br. s., 1H), 7.16 (d, J=2.0 Hz, 1H), 3.95 (quin, J=7.3 Hz, 2H), 3.77 (s, 3H), 3.22-3.27 (m, 2H), 2.81 (d, J=5.1 Hz, 3H), 1.18 (t, J=6.9 Hz, 3H). MS (ESI): m/z 653.02/655.02 [M+H]+. UPLC: tR=0.89 min (polar—2 min).

Workup

  1. customtR=0.89 min (polar—2 min)

Sources & evidence

ORD record
ord-d9f827f5c3744b91a2de672986e4819d
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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