2,2-Dimethyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propan-1-ol → HCID 178485576, compound

HRID 2279890Notes

Reaction equation

HRID 2279890 reaction equation
BrC1N=C(C(=O)NC)C(NC2C(C(F)(F)F)=CN=C(NC3C=CC(CCP(=O)OCCCN4C=C(B5OC(C)(C)C(C)(C)O5)C=N4)=CC=3OC)N=2)=CC=1.[Br:54][C:55]1[N:60]=[C:59]([C:61](=[O:64])[NH:62][CH3:63])[C:58]([NH:65][C:66]2[C:71]([C:72]([F:75])([F:74])[F:73])=[CH:70][N:69]=[C:68]([NH:76][C:77]3[CH:87]=[CH:86][C:80]([CH2:81][CH2:82][PH:83](=[O:85])[OH:84])=[CH:79][C:78]=3[O:88][CH3:89])[N:67]=2)=[CH:57][CH:56]=1.[CH3:90][C:91]([CH3:109])([CH2:94][N:95]1[CH:99]=[C:98]([B:100]2[O:104][C:103]([CH3:106])([CH3:105])[C:102]([CH3:108])([CH3:107])[O:101]2)[CH:97]=[N:96]1)[CH2:92]O>>[Br:54][C:55]1[N:60]=[C:59]([C:61](=[O:64])[NH:62][CH3:63])[C:58]([NH:65][C:66]2[C:71]([C:72]([F:75])([F:73])[F:74])=[CH:70][N:69]=[C:68]([NH:76][C:77]3[CH:87]=[CH:86][C:80]([CH2:81][CH2:82][PH:83](=[O:84])[O:85][CH2:90][C:91]([CH3:109])([CH3:92])[CH2:94][N:95]4[CH:99]=[C:98]([B:100]5[O:104][C:103]([CH3:106])([CH3:105])[C:102]([CH3:108])([CH3:107])[O:101]5)[CH:97]=[N:96]4)=[CH:79][C:78]=3[O:88][CH3:89])[N:67]=2)=[CH:57][CH:56]=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 178485575HCID 178485575, compound2×HCID 178485577HCID 178485577, compound

Product 1

HCID 178485576HCID 178485576, compoundYield 19.6%

Procedure

This material was prepared analogously to Compound 61A using (4-{[4-{[6-bromo-2-(methylcarbamoyl)pyridin-3-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)methylphosphinic acid (Compound 61B, 250 mg, 0.42 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, 119 mg, 0.424 mmol) to afford 70 mg of the title compound (19%). MS (ESI): m/z=851.22/853.23 [M+H]+. UPLC: tR=1.17 min (UPLC-TOF: polar—2 min).

Sources & evidence

ORD record
ord-45f1b2ad32ee42a5b2ca74c32c874e96
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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