2,2-Dimethyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propan-1-ol → 2,2-dimethyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propyl propan-2-yl (4-{[4-{[6-bromo-2-(methylcarbamoyl)pyridin-3-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate

HRID 2279916Notes

Reaction equation

HRID 2279916 reaction equation
BrC1N=C(C(=O)NC)C(NC2C(C(F)(F)F)=CN=C(NC3C=CC(CP(=O)(O[C@@H](CCN4C=C(B5OC(C)(C)C(C)(C)O5)C=N4)C)OCC)=CC=3OC)N=2)=CC=1.[Br:57][C:58]1[N:63]=[C:62]([C:64](=[O:67])[NH:65][CH3:66])[C:61]([NH:68][C:69]2[C:74]([C:75]([F:78])([F:77])[F:76])=[CH:73][N:72]=[C:71]([NH:79][C:80]3[CH:93]=[CH:92][C:83]([CH2:84][P:85](=[O:91])([OH:90])[O:86][CH:87]([CH3:89])[CH3:88])=[CH:82][C:81]=3[O:94][CH3:95])[N:70]=2)=[CH:60][CH:59]=1.[CH3:96][C:97]([CH3:115])([CH2:100][N:101]1[CH:105]=[C:104]([B:106]2[O:110][C:109]([CH3:112])([CH3:111])[C:108]([CH3:114])([CH3:113])[O:107]2)[CH:103]=[N:102]1)[CH2:98]O>>[Br:57][C:58]1[N:63]=[C:62]([C:64](=[O:67])[NH:65][CH3:66])[C:61]([NH:68][C:69]2[C:74]([C:75]([F:78])([F:76])[F:77])=[CH:73][N:72]=[C:71]([NH:79][C:80]3[CH:93]=[CH:92][C:83]([CH2:84][P:85](=[O:90])([O:86][CH:87]([CH3:88])[CH3:89])[O:91][CH2:96][C:97]([CH3:115])([CH3:98])[CH2:100][N:101]4[CH:105]=[C:104]([B:106]5[O:110][C:109]([CH3:112])([CH3:111])[C:108]([CH3:114])([CH3:113])[O:107]5)[CH:103]=[N:102]4)=[CH:82][C:81]=3[O:94][CH3:95])[N:70]=2)=[CH:60][CH:59]=1

Participants

4

Reactant 3

HCID 678124422,2-Dimethyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propan-1-ol2×HCID 86697847ethyl (2R)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]butan-2-yl (4-{[4-{[6-bromo-2-(methylcarbamoyl)pyridin-3-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonateHCID 86697851Propan-2-yl hydrogen (4-{[4-{[6-bromo-2-(methylcarbamoyl)pyridin-3-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate2×

Product 1

HCID 866978562,2-dimethyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propyl propan-2-yl (4-{[4-{[6-bromo-2-(methylcarbamoyl)pyridin-3-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonateYield 40%

Procedure

Racemic Compound 73A was prepared analogously to Compound 69A by using propan-2-yl hydrogen (4-{[4-{[6-bromo-2-(methylcarbamoyl)pyridin-3-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate (Compound 72B, 265 mg, 0.418 mmol) and 2,2-dimethyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propan-1-ol (Compound 47B, 117 mg, 0.418 mmol) to afford 149 mg of the title compound (40%). MS (ESI): m/z=895.81/897.83 [M+H]+. UPLC: tR=1.77 min (UPLC-TOF: polar—2 min).

Sources & evidence

ORD record
ord-9574e938f59e4ff8ad7c59962a622668
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

Loading…