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-({6-[3-cyano-1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-2-(methylcarbamoyl)pyridin-3-yl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate

HRID 2279854Notes

Reaction equation

HRID 2279854 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.[C:50]([C:52]1[C:56]([C:57]2[N:62]=[C:61]([C:63](=[O:66])[NH:64][CH3:65])[C:60]([NH:67][C:68]3[C:73]([C:74]([F:77])([F:76])[F:75])=[CH:72][N:71]=[C:70]([NH:78][C:79]4[CH:93]=[CH:92][C:82]([CH2:83][P:84](=[O:91])([O:88]CC)[O:85][CH2:86][CH3:87])=[CH:81][C:80]=4[O:94][CH3:95])[N:69]=3)=[CH:59][CH:58]=2)=[CH:55][N:54]([CH2:96][CH2:97][CH2:98][OH:99])[N:53]=1)#[N:51]>>[C:50]([C:52]1[C:56]([C:57]2[N:62]=[C:61]([C:63](=[O:66])[NH:64][CH3:65])[C:60]([NH:67][C:68]3[C:73]([C:74]([F:77])([F:75])[F:76])=[CH:72][N:71]=[C:70]([NH:78][C:79]4[CH:93]=[CH:92][C:82]([CH2:83][P:84](=[O:88])([OH:91])[O:85][CH2:86][CH3:87])=[CH:81][C:80]=4[O:94][CH3:95])[N:69]=3)=[CH:59][CH:58]=2)=[CH:55][N:54]([CH2:96][CH2:97][CH2:98][OH:99])[N:53]=1)#[N:51]

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 86697792diethyl (4-{[4-({6-[3-cyano-1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-2-(methylcarbamoyl)pyridin-3-yl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate2×

Product 1

HCID 131733493ethyl hydrogen (4-{[4-({6-[3-cyano-1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-2-(methylcarbamoyl)pyridin-3-yl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonateYield 100.4%

Procedure

Prepared analogously to Compound 3A using diethyl (4-{[4-({6-[3-cyano-1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-2-(methylcarbamoyl)pyridin-3-yl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate (Compound 52B, 259 mg, 0.361 mmol) to afford 250 mg of the title compound (100%). 1H NMR (400 MHz, CD3OD) δ 9.09 (d, J=7.8 Hz, 1H), 8.88 (br. s., 1H), 8.30 (s, 1H), 7.86 (d, J=9.1 Hz, 1H), 7.51 (br. s., 1H), 7.11 (s, 1H), 6.97 (d, J=7.8 Hz, 1H), 4.39 (t, J=6.8 Hz, 2H), 3.83-3.94 (m, 5H), 3.62 (t, J=5.9 Hz, 2H), 3.00-3.08 (m, 2H), 2.97 (s, 3H), 2.10-2.20 (m, 2H), 1.14 (t, J=7.1 Hz, 3H). MS (ESI): m/z=690.49 [M+H]+. UPLC: tR=1.26 min (UPLC-TOF: polar—2 min).

Sources & evidence

ORD record
ord-4c1b708855f9410b95696126be8eb5e8
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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