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-methyl-2-(methylcarbamoyl)phenyl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate

HRID 2279789Notes

Reaction equation

HRID 2279789 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[CH3:98])[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:73])([F:74])[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[CH3:98])[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 86697738Diethyl (4-{[4-({4-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-3-methyl-2-(methyl carbamoyl)phenyl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate2×

Product 1

HCID 86697737Ethyl hydrogen (4-{[4-({4-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-3-methyl-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-methyl-2-(methyl carbamoyl)phenyl}amino)-5-(trifluoromethyl) pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate (Compound 29B). 1H NMR (CD3OD, 400 MHz): δ 8.25 (s, 1H), 7.92 (s, 1H), 7.79 (d, J=8.1 Hz, 1H), 7.69 (s, 1H), 7.64 (d, J=8.3 Hz, 1H), 7.46 (d, J=8.4 Hz, 1H), 6.99 (s, 1H), 6.59 (d, J=6.8 Hz, 1H), 4.35 (t, J=6.8 Hz, 2H), 3.88 (s, 3H), 3.79 (m, 2H), 3.60 (t, J=6.1 Hz, 2H), 2.87 (d, J=21.5 Hz, 2H), 2.85 (s, 3H), 2.36 (s, 3H), 2.12 (m, 2H), 1.13 (t, J=7.1 Hz, 3H). MS (ESI): m/z=678.23 [M+H]+. UPLC: tR=1.03 min (UPLC-TOF: polar—3 min).

Workup

  1. customtR=1.03 min (UPLC-TOF: polar—3 min)

Sources & evidence

ORD record
ord-a8e1837759c14e5593cada5b079e56d7
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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