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 → HCID 86697705, compound

HRID 2279751Notes

Reaction equation

HRID 2279751 reaction equation
[CH2:1](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)[CH3:2].[OH:50][CH2:51][CH2:52][CH2:53][CH2:54][N:55]1[CH:59]=[C:58]([C:60]2[N:65]=[C:64]([C:66](=[O:69])[NH:67][CH3:68])[C:63]([NH:70][C:71]3[C:76]([C:77]([F:80])([F:79])[F:78])=[CH:75][N:74]=[C:73]([NH:81][C:82]4[CH:92]=[CH:91][C:85]([CH2:86][P:87](=[O:90])([O-:89])[O-:88])=[CH:84][CH:83]=4)[N:72]=3)=[CH:62][CH:61]=2)[CH:57]=[N:56]1>>[OH:50][CH2:51][CH2:52][CH2:53][CH2:54][N:55]1[CH:59]=[C:58]([C:60]2[N:65]=[C:64]([C:66](=[O:69])[NH:67][CH3:68])[C:63]([NH:70][C:71]3[C:76]([C:77]([F:79])([F:80])[F:78])=[CH:75][N:74]=[C:73]([NH:81][C:82]4[CH:83]=[CH:84][C:85]([CH2:86][P:87](=[O:89])([OH:88])[O:90][CH2:1][CH3:2])=[CH:91][CH:92]=4)[N:72]=3)=[CH:62][CH:61]=2)[CH:57]=[N:56]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 86697706HCID 86697706, compound2×

Product 1

HCID 86697705HCID 86697705, compoundYield 90%

Procedure

Prepared analogously to Compound 3A using (4-{[4-({6-[1-(4-hydroxybutyl)-1H-pyrazol-4-yl]-2-(methylcarbamoyl)pyridin-3-yl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate (Compound 16B, 127 mg, 188 μmol) to afford 109 mg of the title compound (90%). 1H NMR (400 MHz, CD3OD) δ 9.16 (br. s., 1H), 8.44 (br. s., 1H), 8.28 (s, 1H), 8.15-8.19 (m, 1H), 7.67 (d, J=8.8 Hz, 1H), 7.44 (dd, J=2.6, 7.9 Hz, 2H), 7.33 (dd, J=1.9, 8.5 Hz, 2H), 4.22 (t, J=7.1 Hz, 2H), 3.86 (quin, J=7.0 Hz, 2H), 3.57-3.63 (m, 2H), 3.03 (s, 1H), 2.94-3.00 (m, 4H), 1.92-2.05 (m, 2H), 1.50-1.64 (m, 2H), 1.16 (t, J=7.1 Hz, 3H). MS (ESI): m/z 649.75 [M+H]+. UPLC: tR=1.10 min (UPLC-SQD: analytical—2 min).

Sources & evidence

ORD record
ord-fb44a4ce21494a5ca5fd24241068f2c6
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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