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 → Diethyl (4-{[4-{[6-bromo-2-(methylcarbamoyl)pyridin-3-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-2-chloro-3-methoxybenzyl)phosphonate

HRID 2279862Notes

Reaction equation

HRID 2279862 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:50][C:51]1[C:65]([O:66][CH3:67])=[C:64]([NH:68][C:69]2[N:74]=[C:73](Cl)[C:72]([C:76]([F:79])([F:78])[F:77])=[CH:71][N:70]=2)[CH:63]=[CH:62][C:52]=1[CH2:53][P:54](=[O:61])([O:58][CH2:59][CH3:60])[O:55][CH2:56][CH3:57].[NH2:80][C:81]1[C:82]([C:88]([NH:90][CH3:91])=[O:89])=[N:83][C:84]([Br:87])=[CH:85][CH:86]=1>>[Br:87][C:84]1[N:83]=[C:82]([C:88](=[O:89])[NH:90][CH3:91])[C:81]([NH:80][C:73]2[C:72]([C:76]([F:79])([F:78])[F:77])=[CH:71][N:70]=[C:69]([NH:68][C:64]3[CH:63]=[CH:62][C:52]([CH2:53][P:54](=[O:61])([O:58][CH2:59][CH3:60])[O:55][CH2:56][CH3:57])=[C:51]([Cl:50])[C:65]=3[O:66][CH3:67])[N:74]=2)=[CH:86][CH:85]=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-methylpicolinamideHCID 86697800Diethyl 2-chloro-4-(4-chloro-5-(trifluoromethyl)pyrimidin-2-ylamino)-3-methoxybenzylphosphonate2×

Product 1

HCID 86697799Diethyl (4-{[4-{[6-bromo-2-(methylcarbamoyl)pyridin-3-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-2-chloro-3-methoxybenzyl)phosphonate

Procedure

Prepared analogously to Compound 1B with diethyl (2-chloro-4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate (Compound 54D) and compound 6D. MS (ESI): m/z 681.34/683.34 [M+H]+. UPLC: tR=1.51 min (UPLC-SQD: analytical—2 min).

Workup

  1. customtR=1.51 min (UPLC-SQD: analytical—2 min)

Sources & evidence

ORD record
ord-f2fdd3f1b397468a8e73dceb715ef606
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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