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-[1-(3-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-2-(methylcarbamoyl)pyridin-3-yl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate

HRID 2279759Notes

Reaction equation

HRID 2279759 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][CH:52]([CH3:98])[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])[N:71]=3)=[CH:61][CH:60]=2)[CH:56]=[N:55]1>>[OH:50][CH2:51][CH:52]([CH3:98])[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:77])[F:78])=[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])[N: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 86697712HCID 86697712, compound2×

Product 1

HCID 86697711Ethyl hydrogen (4-{[4-({6-[1-(3-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-2-(methylcarbamoyl)pyridin-3-yl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate

Procedure

Prepared analogously to Compound 3A using diethyl (4-{[4-({6-[1-(3-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-2-(methylcarbamoyl)pyridin-3-yl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate (Compound 18B): 1H NMR (CD3OD, 400 MHz): δ=9.02 (br. s., 1H), 8.52 (s, 1H), 8.32 (s, 1H), 8.25 (s, 1H), 7.75 (d, J=8.8 Hz, 1H), 7.64 (br. s., 1H), 7.12 (s, 1H), 6.98-6.92 (m, 1H), 4.29 (dd, J=6.7, 13.5 Hz, 1H), 4.08 (dd, J=7.1, 13.6 Hz, 1H), 3.92-3.83 (m, 5H), 3.48 (d, J=5.8 Hz, 2H), 3.03 (d, J=21.0 Hz, 2H), 2.99 (s, 3H), 2.33-2.23 (m, 1H), 1.15 (t, J=7.1 Hz, 3H), 0.95 (d, J=7.1 Hz, 3H). MS (ESI): m/z=679.75 [M+H]+. UPLC: tR=1.16 min (UPLC-SQD: analytical—2 min).

Workup

  1. customtR=1.16 min (UPLC-SQD: analytical—2 min)

Sources & evidence

ORD record
ord-035d4eb9e12048c7bd24879db68324c4
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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