Diethyl (4-{[4-({7-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate → HCID 178476795, compound

HRID 2279888Notes

Reaction equation

HRID 2279888 reaction equation
OCCCN1C=C(C2C=CC(NC3C(C(F)(F)F)=CN=C(NC4C=CC(CP(=O)(OCC)OCC)=CC=4OC)N=3)=C3C=2CN(C)C3=O)C=N1.Cl[C:51]1[C:56]([C:57]([F:60])([F:59])[F:58])=[CH:55][N:54]=[C:53]([NH:61][C:62]2[CH:74]=[CH:73][C:65]([CH2:66][CH2:67][PH:68](=[O:72])[O:69][CH2:70][CH3:71])=[CH:64][C:63]=2[O:75][CH3:76])[N:52]=1.[NH2:77][C:78]1[C:79]([C:85]([NH:87][CH3:88])=[O:86])=[N:80][C:81]([Br:84])=[CH:82][CH:83]=1>>[Br:84][C:81]1[N:80]=[C:79]([C:85](=[O:86])[NH:87][CH3:88])[C:78]([NH:77][C:51]2[C:56]([C:57]([F:60])([F:59])[F:58])=[CH:55][N:54]=[C:53]([NH:61][C:62]3[CH:74]=[CH:73][C:65]([CH2:66][CH2:67][PH:68](=[O:72])[O:69][CH2:70][CH3:71])=[CH:64][C:63]=3[O:75][CH3:76])[N:52]=2)=[CH:83][CH:82]=1

Participants

4

Reactant 3

HCID 58292892Diethyl (4-{[4-({7-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonateHCID 866976863-Amino-6-bromo-N-methylpicolinamide2×HCID 178476793HCID 178476793, compound2×

Product 1

HCID 178476795HCID 178476795, compoundYield 76%

Procedure

Prepared analogously to Compound 1B using ethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)methylphosphinate (Compound 61 D, 270 mg, 0.64 mmol) and 3-amino-6-bromo-N-methylpyridine-2-carboxamide (Compound 6D, 154 mg, 0.669 mmol) to afford 298 mg of the title compound (76%). 1H NMR (400 MHz, CD-3OD) δ 9.00 (br. s., 1H), 8.36 (s, 1H), 7.63-7.73 (m, 1H), 7.51-7.61 (m, 1H), 7.07 (t, J=1.9 Hz, 1H), 6.93 (td, J=2.2, 8.1 Hz, 1H), 4.04-4.16 (m, 2H), 3.89 (s, 3H), 3.33 (s, 1H), 3.29 (s, 1H), 2.93 (s, 3H), 1.51 (s, 3H), 1.33 (t, J=7.1 Hz, 3H). MS (ESI): m/z=617.06/619.06 [M+H]+. HPLC: tR=1.01 min (UPLC-TOF: polar—3 min).

Sources & evidence

ORD record
ord-cbdcb9cf025d4b42894fdd396f9c06f2
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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