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-hydroxypropyl)-1H-pyrazol-4-yl]-2-(methylcarbamoyl)pyridin-3-yl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methylbenzyl)phosphonate

HRID 2279806Notes

Reaction equation

HRID 2279806 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[CH3:96])[N: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:78])([F:79])[F:77])=[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[CH3:96])[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 86697747diethyl (4-{[4-({6-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-2-(methylcarbamoyl)pyridin-3-yl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methyl benzyl)phosphonate2×

Product 1

HCID 86697746Ethyl hydrogen (4-{[4-({6-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-2-(methylcarbamoyl)pyridin-3-yl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methylbenzyl)phosphonateYield 99.8%

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)pyrimidin-2-yl]amino}-3-methylbenzyl)phosphonate (Compound 33B, 345 mg, 510 μmol) to afford 330 mg of the title compound (99.8%). 1H NMR (400 MHz, CD3OD) δ 8.71-8.96 (m, 1H), 8.60 (s, 1H), 8.28 (s, 1H), 8.23 (s, 1H), 7.63 (d, J=9.1 Hz, 1H), 7.34 (s, 1H), 7.22-7.28 (m, 2H), 4.32 (t, J=6.8 Hz, 2H), 3.88 (t, J=7.0 Hz, 2H), 3.59 (t, J=6.1 Hz, 2H), 3.06 (d, J=21.9 Hz, 2H), 2.98 (s, 3H), 2.23 (s, 3H), 2.11 (t, J=6.3 Hz, 2H), 1.12 (t, J=7.1 Hz, 3H). MS (ESI): m/z=649.65 [M+H]+. UPLC: tR=1.06 min (UPLC-SQD: analytical—2 min).

Sources & evidence

ORD record
ord-38c8efbfe5b8488da7c99012d696c7b3
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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