(1-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]methyl}cyclopropyl)methanol → ethyl (1-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]methyl}cyclopropyl)methyl (4-{[4-{[6-bromo-2-(methylcarbamoyl)pyridin-3-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate

HRID 2279891Notes

Reaction equation

HRID 2279891 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:89]=[CH:88][C:80]([CH2:81][P:82](=[O:87])([OH:86])[O:83][CH2:84][CH3:85])=[CH:79][C:78]=3[O:90][CH3:91])[N:67]=2)=[CH:57][CH:56]=1.[CH3:92][C:93]1([CH3:111])[C:97]([CH3:99])([CH3:98])[O:96][B:95]([C:100]2[CH:101]=[N:102][N:103]([CH2:105][C:106]3([CH2:109]O)[CH2:108][CH2:107]3)[CH:104]=2)[O:94]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:73])[F:74])=[CH:70][N:69]=[C:68]([NH:76][C:77]3[CH:89]=[CH:88][C:80]([CH2:81][P:82](=[O:86])([O:87][CH2:109][C:106]4([CH2:105][N:103]5[CH:104]=[C:100]([B:95]6[O:94][C:93]([CH3:111])([CH3:92])[C:97]([CH3:99])([CH3:98])[O:96]6)[CH:101]=[N:102]5)[CH2:108][CH2:107]4)[O:83][CH2:84][CH3:85])=[CH:79][C:78]=3[O:90][CH3:91])[N:67]=2)=[CH:57][CH:56]=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 86697762Ethyl hydrogen (4-{[4-{[6-bromo-2-(methylcarbamoyl)pyridin-3-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate2×HCID 178485577HCID 178485577, compound

Product 1

HCID 86697828ethyl (1-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]methyl}cyclopropyl)methyl (4-{[4-{[6-bromo-2-(methylcarbamoyl)pyridin-3-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonateYield 61.5%

Procedure

Prepared analogously to Compound 61A using ethyl hydrogen (4-{[4-{[6-bromo-2-(methylcarbamoyl)pyridin-3-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate (Compound 38C, 670 mg, 1.1 mmol) and (1-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]methyl}cyclopropyl)methanol (Compound 63B, 300 mg, 1.08 mmol) to afford 584 mg of the title compound as a racemic mixture (62%). 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-86fc9a6a280c42c1985b64ed614cc622
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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