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-3-methoxybenzyl)phosphonate

HRID 2279861Notes

Reaction equation

HRID 2279861 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[CH:76]=[CH:75][C:65]([CH2:66][P:67](=[O:74])([O:71]CC)[O:68][CH2:69][CH3:70])=[C:64]([Cl:77])[C:63]=3[O:78][CH3:79])[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:59])([F:58])[F:60])=[CH:55][N:54]=[C:53]([NH:61][C:62]3[CH:76]=[CH:75][C:65]([CH2:66][P:67](=[O:71])([OH:74])[O:68][CH2:69][CH3:70])=[C:64]([Cl:77])[C:63]=3[O:78][CH3:79])[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 86697799Diethyl (4-{[4-{[6-bromo-2-(methylcarbamoyl)pyridin-3-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-2-chloro-3-methoxybenzyl)phosphonate2×

Product 1

HCID 86697798Ethyl hydrogen (4-{[4-{[6-bromo-2-(methylcarbamoyl)pyridin-3-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-2-chloro-3-methoxybenzyl)phosphonate

Procedure

Prepared analogously to Compound 38C with diethyl (4-{[4-{[6-bromo-2-(methylcarbamoyl)pyridin-3-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-2-chloro-3-methoxybenzyl)phosphonate (Compound 54C). MS (ESI): m/z 653.03/655.02 [M+H]+. UPLC: tR=0.98 min (UPLC-TOF: polar—2 min).

Workup

  1. customtR=0.98 min (UPLC-TOF: polar—2 min)

Sources & evidence

ORD record
ord-ad23ef2dc7c049c5ac804a49a14b2028
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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