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 86697788, compound

HRID 2279852Notes

Reaction equation

HRID 2279852 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[N:55]([CH2:56][CH2:57][CH2:58][OH:59])[N:54]=[CH:53][C:52]=1[C:60]1[N:65]=[C:64]([C:66](=[O:69])[NH:67][CH3:68])[C:63]([NH:70][C:71]2[C:76]([C:77]([F:80])([F:79])[F:78])=[CH:75][N:74]=[C:73]([NH:81][C:82]3[CH:96]=[CH:95][C:85]([CH2:86][P:87](=[O:94])([O:91]CC)[O:88][CH2:89][CH3:90])=[CH:84][C:83]=3[O:97][CH3:98])[N:72]=2)=[CH:62][CH:61]=1>>[Cl:50][C:51]1[N:55]([CH2:56][CH2:57][CH2:58][OH:59])[N:54]=[CH:53][C:52]=1[C:60]1[N:65]=[C:64]([C:66](=[O:69])[NH:67][CH3:68])[C:63]([NH:70][C:71]2[C:76]([C:77]([F:78])([F:79])[F:80])=[CH:75][N:74]=[C:73]([NH:81][C:82]3[CH:96]=[CH:95][C:85]([CH2:86][P:87](=[O:91])([OH:94])[O:88][CH2:89][CH3:90])=[CH:84][C:83]=3[O:97][CH3:98])[N:72]=2)=[CH:62][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 86697789HCID 86697789, compound2×

Product 1

HCID 86697788HCID 86697788, compoundYield 83.1%

Procedure

Prepared analogously to Compound 3A using diethyl (4-{[4-({6-[5-chloro-1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-2-(methylcarbamoyl)pyridin-3-yl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate (Compound 51B, 161 mg, 0.222 mmol) to afford 129 mg of the title compound (83%). 1H NMR (400 MHz, CD3OD) δ 9.05 (br. s., 1H), 8.29-8.35 (m, 2H), 7.81 (d, J=8.8 Hz, 1H), 7.69 (d, J=7.3 Hz, 1H), 7.12 (s, 1H), 6.90 (d, J=8.1 Hz, 1H), 4.35 (t, J=7.1 Hz, 2H), 3.79-3.92 (m, 5H), 3.59-3.65 (m, 2H), 3.03 (s, 1H), 2.95 (s, 4H), 2.09 (quin, J=6.6 Hz, 2H), 1.16 (t, J=6.9 Hz, 3H). MS (ESI): m/z=699.54/701.60 [M+H]+. UPLC: tR=1.21 min (UPLC-TOF: polar—2 min).

Sources & evidence

ORD record
ord-b1fffb6a90554c139d732da13dae55fe
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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