3-{5-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1H-imidazol-2-yl}-2-azabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester → 3-(5-{4-[6-(2-{1-[2-Methoxycarbonylamino-2-(tetrahydro-pyran-4-yl)-acetyl]-pyrrolidin-2-yl}-3H-imidazol-4-yl)-naphthalen-2-yl]-phenyl}-1H-imidazol-2-yl)-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

HRID 1751493Notes

Reaction equation

C(OC(N1CC(=C)CC1C1NC(C2C=CC(C3C=CC4C(=CC=C(C5NC(C6CCCN6C(=O)C(NC(OC)=O)C(C)C)=NC=5)C=4)C=3)=CC=2)=CN=1)=O)(C)(C)C.[CH3:56][O:57][C:58](=[O:90])[NH:59][CH:60]([CH:84]1[CH2:89][CH2:88][O:87][CH2:86][CH2:85]1)[C:61]([N:63]1[CH2:67][CH2:66][CH2:65][CH:64]1[C:68]1[NH:69][C:70]([C:73]2[CH:82]=[CH:81][C:80]3[C:75](=[CH:76][CH:77]=[C:78](Br)[CH:79]=3)[CH:74]=2)=[CH:71][N:72]=1)=[O:62].[C:91]([O:95][C:96]([N:98]1[CH:103]([C:104]2[NH:105][C:106]([C:109]3[CH:114]=[CH:113][C:112](B4OC(C)(C)C(C)(C)O4)=[CH:111][CH:110]=3)=[CH:107][N:108]=2)[CH:102]2[CH2:124][CH:99]1[CH2:100][CH2:101]2)=[O:97])([CH3:94])([CH3:93])[CH3:92]>>[C:91]([O:95][C:96]([N:98]1[CH:103]([C:104]2[NH:105][C:106]([C:109]3[CH:110]=[CH:111][C:112]([C:78]4[CH:77]=[CH:76][C:75]5[C:80](=[CH:81][CH:82]=[C:73]([C:70]6[NH:69][C:68]([CH:64]7[CH2:65][CH2:66][CH2:67][N:63]7[C:61](=[O:62])[CH:60]([NH:59][C:58]([O:57][CH3:56])=[O:90])[CH:84]7[CH2:89][CH2:88][O:87][CH2:86][CH2:85]7)=[N:72][CH:71]=6)[CH:74]=5)[CH:79]=4)=[CH:113][CH:114]=3)=[CH:107][N:108]=2)[CH:102]2[CH2:124][CH:99]1[CH2:100][CH2:101]2)=[O:97])([CH3:94])([CH3:93])[CH3:92]

Participants

Reactant 3

HCID 666205563-{5-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1H-imidazol-2-yl}-2-azabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

HCID 696727712-{5-[4-(6-{2-[1-(2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-naphthalen-2-yl)-phenyl]-1H-imidazol-2-yl}-4-methylene-pyrrolidine-1-carboxylic acid tert-butyl ester

HCID 69675007[2-{2-[5-(6-Bromo-naphthalen-2-yl)-1H-imidazol-2-yl]-pyrrolidin-1-yl}-2-oxo-1-(tetrahydro-pyran-4-yl)-ethyl]-carbamic acid methyl ester

Product 1

HCID 696754323-(5-{4-[6-(2-{1-[2-Methoxycarbonylamino-2-(tetrahydro-pyran-4-yl)-acetyl]-pyrrolidin-2-yl}-3H-imidazol-4-yl)-naphthalen-2-yl]-phenyl}-1H-imidazol-2-yl)-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl esterYield 48%

Procedure

This compound was synthesized using the same procedure used to make 2-{5-[4-(6-{2-[1-(2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-naphthalen-2-yl)-phenyl]-1H-imidazol-2-yl}-4-methylene-pyrrolidine-1-carboxylic acid tert-butyl ester using [2-{2-[5-(6-Bromo-naphthalen-2-yl)-1H-imidazol-2-yl]-pyrrolidin-1-yl}-2-oxo-1-(tetrahydro-pyran-4-yl)-ethyl]-carbamic acid methyl ester (0.150 g, 0.277 mmol) and 3-{5-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1H-imidazol-2-yl}-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (0.155 g, 0.332 mmol) to give 3-(5-{4-[6-(2-{1-[2-Methoxycarbonylamino-2-(tetrahydro-pyran-4-yl)-acetyl]-pyrrolidin-2-yl}-3H-imidazol-4-yl)-naphthalen-2-yl]-phenyl}-1H-imidazol-2-yl)-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (0.106 g, 48% yield). LCMS-ESI+: calc'd for C46H53FN7O6: 799.41 (M+); Found: 800.85 (M+H+).

Workup

customThis compound was synthesized

Sources & evidence

ORD record: ord-016a39bb25f54b90b6b8947c0a9e1ef7
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156823B2

Reaction notes

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