(1-{2-[5-(6-Bromonaphthalen-2-yl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester → [1-(2-{5-[6-(4-{2-[2-(2-Methoxycarbonylamino-3-methyl-butyryl)-2-aza-bicyclo[2.2.1]hept-3-yl]-3H-imidazol-4-yl}-phenyl)-naphthalen-2-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-carbamic acid methyl ester

HRID 1751500Notes

Reaction equation

HRID 1751500 reaction equation
[CH3:1][O:2][C:3](=[O:32])[NH:4][CH:5]([C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16]1[NH:17][C:18]([C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[C:26](Br)[CH:27]=3)[CH:22]=2)=[CH:19][N:20]=1)=[O:10])[CH:6]([CH3:8])[CH3:7].C(OC(N1CCCC1C1NC(C2C=CC3C(=CC=C([C:60]4[CH:65]=[CH:64][C:63]([C:66]5[NH:67][C:68]([CH:71]6[CH:76]7[CH2:77][CH:73]([CH2:74][CH2:75]7)[N:72]6[C:78](=[O:88])[CH:79]([NH:83][C:84]([O:86][CH3:87])=[O:85])[CH:80]([CH3:82])[CH3:81])=[N:69][CH:70]=5)=[CH:62][CH:61]=4)C=3)C=2)=CN=1)=O)(C)(C)C>>[CH3:1][O:2][C:3](=[O:32])[NH:4][CH:5]([C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16]1[NH:17][C:18]([C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[C:26]([C:60]4[CH:61]=[CH:62][C:63]([C:66]5[NH:67][C:68]([CH:71]6[CH:76]7[CH2:77][CH:73]([CH2:74][CH2:75]7)[N:72]6[C:78](=[O:88])[CH:79]([NH:83][C:84]([O:86][CH3:87])=[O:85])[CH:80]([CH3:82])[CH3:81])=[N:69][CH:70]=5)=[CH:64][CH:65]=4)[CH:27]=3)[CH:22]=2)=[CH:19][N:20]=1)=[O:10])[CH:6]([CH3:8])[CH3:7]

Participants

3

Reactant 2

HCID 66620357(1-{2-[5-(6-Bromonaphthalen-2-yl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl esterHCID 696751892-{5-[6-(4-{2-[2-(2-Methoxycarbonylamino-3-methyl-butyryl)-2-aza-bicyclo[2.2.1]hept-3-yl]-3H-imidazol-4-yl}-phenyl)-naphthalen-2-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 66621154[1-(2-{5-[6-(4-{2-[2-(2-Methoxycarbonylamino-3-methyl-butyryl)-2-aza-bicyclo[2.2.1]hept-3-yl]-3H-imidazol-4-yl}-phenyl)-naphthalen-2-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-carbamic acid methyl esterYield 24%

Procedure

This compound was synthesized using the procedure used to make (1-{2-[5-(6-Bromo-naphthalen-2-yl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester using 2-{5-[6-(4-{2-[2-(2-Methoxycarbonylamino-3-methyl-butyryl)-2-aza-bicyclo[2.2.1]hept-3-yl]-3H-imidazol-4-yl}-phenyl)-naphthalen-2-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester (0.154 g, 0.203 mmol) giving the title compound (0.041 g, 24% yield) as a white solid. LCMS-ESI+: calc'd for C46H54N8O6: 814.42 (M+); Found: 815.49 (M+H+).

Workup

  1. customThis compound was synthesized

Sources & evidence

ORD record
ord-65c331f9691945e4b9da3fedb28a60fd
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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