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 86697721, compound
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.[F:50][C:51]1[CH:52]=[C:53]([CH:63]=[CH:64][C:65]=1[NH:66][C:67]1[N:72]=[C:71]([NH:73][C:74]2[C:75]([C:90](=[O:93])[NH:91][CH3:92])=[N:76][C:77]([C:80]3[CH:81]=[N:82][N:83]([CH2:85][CH2:86][CH2:87][CH2:88][OH:89])[CH:84]=3)=[CH:78][CH:79]=2)[C:70]([C:94]([F:97])([F:96])[F:95])=[CH:69][N:68]=1)[CH2:54][P:55](=[O:62])([O:59]CC)[O:56][CH2:57][CH3:58]>>[F:50][C:51]1[CH:52]=[C:53]([CH:63]=[CH:64][C:65]=1[NH:66][C:67]1[N:72]=[C:71]([NH:73][C:74]2[C:75]([C:90](=[O:93])[NH:91][CH3:92])=[N:76][C:77]([C:80]3[CH:81]=[N:82][N:83]([CH2:85][CH2:86][CH2:87][CH2:88][OH:89])[CH:84]=3)=[CH:78][CH:79]=2)[C:70]([C:94]([F:97])([F:95])[F:96])=[CH:69][N:68]=1)[CH2:54][P:55](=[O:59])([OH:62])[O:56][CH2:57][CH3:58]Participants
3
Procedure
Prepared analogously to Compound 3A using diethyl (3-fluoro-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 23B, 133 mg, 191 μmol) to afford 115 mg of the title compound (90%). 1H NMR (400 MHz, CD3OD) δ=8.98-9.08 (m, 1H), 8.56 (s, 1H), 8.32 (s, 1H), 8.23 (s, 1H), 7.71 (d, J=8.8 Hz, 1H), 7.51 (t, J=7.8 Hz, 1H), 7.26 (d, J=11.9 Hz, 1H), 7.18 (d, J=8.1 Hz, 1H), 4.24 (t, J=7.1 Hz, 2H), 3.88 (quin, J=7.0 Hz, 2H), 3.60 (t, J=6.4 Hz, 2H), 3.01-3.10 (m, 2H), 2.96-3.00 (m, 3H), 1.93-2.03 (m, 2H), 1.50-2.06 (m, 2H), 1.14 (t, J=7.07 Hz, 3H). MS (ESI): m/z=667.69 [M+H]+. UPLC: tR=1.13 min (UPLC-SQD: analytical—2 min).
Sources & evidence
- ORD record
- ord-c2f4961ce9f8411c92e11556f828b4af
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09133224B2
Reaction notes
Loading…