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

HRID 2279794Notes

Reaction equation

HRID 2279794 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.[OH:50][CH2:51][CH2:52][CH2:53][N:54]1[CH:58]=[C:57]([C:59]2[CH:64]=[CH:63][C:62]([NH:65][C:66]3[C:71]([C:72]([F:75])([F:74])[F:73])=[CH:70][N:69]=[C:68]([NH:76][C:77]4[CH:91]=[CH:90][C:80]([CH2:81][P:82](=[O:89])([O:86]CC)[O:83][CH2:84][CH3:85])=[CH:79][C:78]=4[O:92][CH3:93])[N:67]=3)=[C:61]([C:94](=[O:97])[NH:95][CH3:96])[C:60]=2[O:98][CH3:99])[CH:56]=[N:55]1>>[OH:50][CH2:51][CH2:52][CH2:53][N:54]1[CH:58]=[C:57]([C:59]2[CH:64]=[CH:63][C:62]([NH:65][C:66]3[C:71]([C:72]([F:74])([F:73])[F:75])=[CH:70][N:69]=[C:68]([NH:76][C:77]4[CH:91]=[CH:90][C:80]([CH2:81][P:82](=[O:86])([OH:89])[O:83][CH2:84][CH3:85])=[CH:79][C:78]=4[O:92][CH3:93])[N:67]=3)=[C:61]([C:94](=[O:97])[NH:95][CH3:96])[C:60]=2[O:98][CH3:99])[CH:56]=[N:55]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 86697741diethyl (4-{[4-({4-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-3-methoxy-2-(methyl carbamoyl)phenyl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxy benzyl)phosphonate2×

Product 1

HCID 86697740Ethyl hydrogen (4-{[4-({4-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-3-methoxy-2-(methylcarbamoyl)phenyl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate

Procedure

Prepared analogously to Compound 3A using diethyl (4-{[4-({4-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-3-methoxy-2-(methyl carbamoyl)phenyl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxy benzyl)phosphonate (Compound 30B). 1H NMR (CD3OD, 400 MHz): δ 8.27 (s, 1H), 8.18 (s, 1H), 7.98 (s, 1H), 7.86 (d, J=8.3 Hz, 1H), 7.83 (d, J=7.8 Hz, 1H), 7.66 (d, J=8.8 Hz, 1H), 7.02 (s, 1H), 6.69 (d, J=8.1 Hz, 1H), 4.33 (t, J=6.8 Hz, 2H), 3.88 (s, 3H), 3.82 (m, 2H), 3.64 (s, 3H), 3.59 (t, J=6.1 Hz, 2H), 2.92 (s, 3H), 2.91 (d, J=20.2 Hz, 2H), 2.11 (m, 2H), 1.13 (t, J=7.1 Hz, 3H). MS (ESI): m/z=694.22 [M+H]+. UPLC: tR=1.09 min (UPLC-TOF: polar—3 min).

Workup

  1. customtR=1.09 min (UPLC-TOF: polar—3 min)

Sources & evidence

ORD record
ord-d696c33a41194238b8c2267013c67256
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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