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 86697753, compound

HRID 2279813Notes

Reaction equation

HRID 2279813 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[N:64]=[C:63]([C:65](=[O:68])[NH:66][CH3:67])[C:62]([NH:69][C:70]3[C:75]([C:76]([F:79])([F:78])[F:77])=[CH:74][N:73]=[C:72]([NH:80][C:81]4[CH:95]=[CH:94][C:84]([CH2:85][P:86](=[O:93])([O:90]CC)[O:87][CH2:88][CH3:89])=[CH:83][C:82]=4[O:96][CH3:97])[CH:71]=3)=[CH:61][CH:60]=2)[CH:56]=[N:55]1>>[OH:50][CH2:51][CH2:52][CH2:53][N:54]1[CH:58]=[C:57]([C:59]2[N:64]=[C:63]([C:65](=[O:68])[NH:66][CH3:67])[C:62]([NH:69][C:70]3[C:75]([C:76]([F:77])([F:78])[F:79])=[CH:74][N:73]=[C:72]([NH:80][C:81]4[CH:95]=[CH:94][C:84]([CH2:85][P:86](=[O:90])([OH:93])[O:87][CH2:88][CH3:89])=[CH:83][C:82]=4[O:96][CH3:97])[CH:71]=3)=[CH:61][CH:60]=2)[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 86697754diethyl (4-{[4-({6-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-2-(methylcarbamoyl)pyridin-3-yl}amino)-5-(trifluoromethyl)pyridin-2-yl]amino}-3-methoxybenzyl)phosphonate2×

Product 1

HCID 86697753HCID 86697753, compound

Procedure

Prepared analogously to Compound 3A using diethyl (4-{[4-({6-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-2-(methylcarbamoyl)pyridin-3-yl}amino)-5-(trifluoromethyl)pyridin-2-yl]amino}-3-methoxybenzyl)phosphonate (Compound 36B). 1H NMR (400 MHz, CD3OD) δ 8.39 (s, 1H), 8.20 (s, 1H), 8.17 (s, 1H), 7.92 (d, J=8.8 Hz, 1H), 7.72 (d, J=8.8 Hz, 1H), 7.46 (d, J=7.8 Hz, 1H), 7.08 (t, J=1.8 Hz, 1H), 6.88 (td, J=2.0, 8.1 Hz, 1H), 6.63 (s, 1H), 4.31 (t, J=6.8 Hz, 2H), 3.88 (s, 3H), 3.74 (quin, J=7 Hz, 2H), 3.57 (t, J=6.1 Hz, 2H), 2.89-2.98 (m, 5H), 2.10 (quin, J=6.5 Hz, 2H), 1.03 (t, J=7.1 Hz, 3H). MS (ESI): m/z 664.21 [M+H]+. UPLC: tR=1.06 min (UPLC-TOF: polar—3 min).

Workup

  1. customtR=1.06 min (UPLC-TOF: polar—3 min)

Sources & evidence

ORD record
ord-84f15c97fb674001b6decf2e870dbfd3
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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