(1-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]methyl}cyclopropyl)methanol → HCID 178485571, compound

HRID 2279911Notes

Reaction equation

HRID 2279911 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:91]=[CH:90][C:83]([CH2:84][CH2:85][CH2:86][PH:87](=[O:89])[OH:88])=[CH:82][C:81]=3[O:92][CH3:93])[N:70]=2)=[CH:60][CH:59]=1.[CH3:94][C:95]1([CH3:113])[C:99]([CH3:101])([CH3:100])[O:98][B:97]([C:102]2[CH:103]=[N:104][N:105]([CH2:107][C:108]3([CH2:111]O)[CH2:110][CH2:109]3)[CH:106]=2)[O:96]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:76])[F:77])=[CH:73][N:72]=[C:71]([NH:79][C:80]3[CH:91]=[CH:90][C:83]([CH2:84][CH2:85][CH2:86][PH:87](=[O:88])[O:89][CH2:111][C:108]4([CH2:107][N:105]5[CH:106]=[C:102]([B:97]6[O:96][C:95]([CH3:113])([CH3:94])[C:99]([CH3:101])([CH3:100])[O:98]6)[CH:103]=[N:104]5)[CH2:110][CH2:109]4)=[CH:82][C:81]=3[O:92][CH3:93])[N:70]=2)=[CH:60][CH:59]=1

Participants

4

Reactant 3

HCID 67811260(1-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]methyl}cyclopropyl)methanol2×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 178485570HCID 178485570, compound2×

Product 1

HCID 178485571HCID 178485571, compoundYield 48%

Procedure

Racemic Compound 71A was prepared analogously to Compound 69A using (4-{[4-{[6-bromo-2-(methylcarbamoyl)pyridin-3-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)ethylphosphinic acid (Compound 67B, 206 mg, 0.341 mmol) and (1-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]methyl}cyclopropyl)methanol (Compound 63B, 400 mg, 2 mmol) to afford 129 mg of the title compound (48%). MS (ESI): m/z=879.92/881.81 [M+H]+. UPLC: tR=1.61 min (UPLC-TOF: polar—2 min).

Sources & evidence

ORD record
ord-2ef34f06da324d9fa4f5ef7ed900578a
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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