Ethyl hydrogen (4-{[4-({2-(diethylcarbamoyl)-4-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]phenyl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate → Ethyl hydrogen (4-{[4-({3-chloro-4-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-2-(methylcarbamoyl)phenyl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxy benzyl)phosphonate

HRID 2279784Notes

Reaction equation

HRID 2279784 reaction equation
C(N(CC)C(C1C=C(C2C=NN(CCCO)C=2)C=CC=1NC1C(C(F)(F)F)=CN=C(NC2C=CC(CP(=O)(O)OCC)=CC=2OC)N=1)=O)C.[Cl:50][C:51]1[C:52]([C:95](=[O:98])[NH:96][CH3:97])=[C:53]([NH:66][C:67]2[C:72]([C:73]([F:76])([F:75])[F:74])=[CH:71][N:70]=[C:69]([NH:77][C:78]3[CH:92]=[CH:91][C:81]([CH2:82][P:83](=[O:90])([O:87]CC)[O:84][CH2:85][CH3:86])=[CH:80][C:79]=3[O:93][CH3:94])[N:68]=2)[CH:54]=[CH:55][C:56]=1[C:57]1[CH:58]=[N:59][N:60]([CH2:62][CH2:63][CH2:64][OH:65])[CH:61]=1>>[Cl:50][C:51]1[C:52]([C:95](=[O:98])[NH:96][CH3:97])=[C:53]([NH:66][C:67]2[C:72]([C:73]([F:75])([F:76])[F:74])=[CH:71][N:70]=[C:69]([NH:77][C:78]3[CH:92]=[CH:91][C:81]([CH2:82][P:83](=[O:87])([OH:90])[O:84][CH2:85][CH3:86])=[CH:80][C:79]=3[O:93][CH3:94])[N:68]=2)[CH:54]=[CH:55][C:56]=1[C:57]1[CH:58]=[N:59][N:60]([CH2:62][CH2:63][CH2:64][OH:65])[CH:61]=1

Participants

3

Reactant 2

HCID 86697678Ethyl hydrogen (4-{[4-({2-(diethylcarbamoyl)-4-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]phenyl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonateHCID 86697734Diethyl (4-{[4-({3-chloro-4-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-2-(methylcarbamoyl)phenyl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxy benzyl)phosphonate2×

Product 1

HCID 86697733Ethyl hydrogen (4-{[4-({3-chloro-4-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-2-(methylcarbamoyl)phenyl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxy benzyl)phosphonateYield 112.1%

Procedure

Prepared analogously to Compound 3A using diethyl (4-{[4-({3-chloro-4-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-2-(methylcarbamoyl)phenyl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate (Compound 28B, 18 mg, 24.8 μmol) to afford 19.4 mg of the title compound. 1H NMR (400 MHz, CD3OD) δ=8.29 (s, 1H), 8.21 (s, 1H), 7.99 (d, J=8.6 Hz, 1H), 7.95 (d, J=1.8 Hz, 1H), 7.81 (d, J=8.1 Hz, 1H), 7.74 (t, J=8.6 Hz, 1H), 7.05 (s, 1H), 6.76 (d, J=8.3 Hz, 1H), 4.33 (t, J=6.8 Hz, 2H), 3.89 (s, 3H), 3.82 (s, 2H), 3.58 (t, J=6.1 Hz, 2H), 2.96 (s, 1H), 2.92 (s, 4H), 2.10 (quin, J=6.51 Hz, 2H), 1.13 (t, J=6.95 Hz, 3H). MS (ESI): m/z=698.19 [M+H]+. UPLC: tR=1.06 min (UPLC-TOF: polar—3 min).

Sources & evidence

ORD record
ord-3ad220ae0fda431f9b0601a50c9888a1
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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