1H-Pyrazole-4-boronic acid → N-((4-(1H-pyrazol-4-yl)-1-trityl-1H-imidazol-2-yl)(5-ethoxy-2-fluoro-3-isopropoxyphenyl)methyl)-4-(5-methyl-1,2,4-oxadiazol-3-yl)benzenamine

HRID 2105035Notes

Reaction equation

HRID 2105035 reaction equation
C(OC1C=C(OC(C)C)C(F)=C(C(C2N(C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)C=C(C3C=CC=CC=3C(F)(F)F)N=2)NC2C=CC(C3N=C(C)ON=3)=CC=2)C=1)C.Br[C:64]1[N:65]=[C:66]([CH:88]([C:102]2[CH:107]=[C:106]([O:108][CH2:109][CH3:110])[CH:105]=[C:104]([O:111][CH:112]([CH3:114])[CH3:113])[C:103]=2[F:115])[NH:89][C:90]2[CH:95]=[CH:94][C:93]([C:96]3[N:100]=[C:99]([CH3:101])[O:98][N:97]=3)=[CH:92][CH:91]=2)[N:67]([C:69]([C:82]2[CH:87]=[CH:86][CH:85]=[CH:84][CH:83]=2)([C:76]2[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=2)[C:70]2[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=2)[CH:68]=1.[NH:116]1[CH:120]=[C:119](B(O)O)[CH:118]=[N:117]1>>[NH:116]1[CH:120]=[C:119]([C:64]2[N:65]=[C:66]([CH:88]([C:102]3[CH:107]=[C:106]([O:108][CH2:109][CH3:110])[CH:105]=[C:104]([O:111][CH:112]([CH3:114])[CH3:113])[C:103]=3[F:115])[NH:89][C:90]3[CH:91]=[CH:92][C:93]([C:96]4[N:100]=[C:99]([CH3:101])[O:98][N:97]=4)=[CH:94][CH:95]=3)[N:67]([C:69]([C:76]3[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=3)([C:70]3[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=3)[C:82]3[CH:83]=[CH:84][CH:85]=[CH:86][CH:87]=3)[CH:68]=2)[CH:118]=[N:117]1

Participants

4

Reactant 3

HCID 177502781H-Pyrazole-4-boronic acidHCID 68813045N-((5-ethoxy-2-fluoro-3-isopropoxyphenyl)(4-(2-(trifluoromethyl)phenyl)-1-trityl-1H-imidazol-2-yl)methyl)-4-(5-methyl-1,2,4-oxadiazol-3-yl)benzenamineHCID 68813809N-((4-bromo-1-trityl-1H-imidazol-2-yl)(5-ethoxy-2-fluoro-3-isopropoxyphenyl)methyl)-4-(5-methyl-1,2,4-oxadiazol-3-yl)benzenamine

Product 1

HCID 68815685N-((4-(1H-pyrazol-4-yl)-1-trityl-1H-imidazol-2-yl)(5-ethoxy-2-fluoro-3-isopropoxyphenyl)methyl)-4-(5-methyl-1,2,4-oxadiazol-3-yl)benzenamineYield 20%

Procedure

According to the procedure for the preparation of Intermediate 77.1, Intermediate 66.3 was coupled with 1H-pyrazol-4-ylboronic acid. The crude product was purified by flash chromatography (0 to 100% EtOAc/hexanes, gradient) to afford 30 mg (20%) of Intermediate 237.1.

Workup

  1. customThe crude product was purified by flash chromatography (0 to 100% EtOAc/hexanes, gradient)

Sources & evidence

ORD record
ord-8595220f6dd640ba956305c6b873f803
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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