[1-(2-{5-[4'-(2-Pyrrolidin-2-yl-3H-imidazol-4-yl)-biphenyl-4-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carbonyl)-3-(2,2,2-trifluoroethoxy)-propyl]-carbamic acid methyl ester → [1-(2-{5-[4'-(2-{1-[2-Methoxycarbonylamino-4-(2,2,2-trifluoro-ethoxy)-butyryl]-pyrrolidin-2-yl}-3H-imidazol-4-yl)-biphenyl-4-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-carbamic acid methyl ester

HRID 72029Notes

Reaction equation

COC(=O)NC(C(N1CCCC1C1NC(C2C=CC(C3C=CC(C4NC(C5CCCN5[C:46](=[O:56])[CH:47]([NH:51][C:52]([O:54][CH3:55])=[O:53])[CH:48]([CH3:50])[CH3:49])=NC=4)=CC=3)=CC=2)=CN=1)=O)CCC(F)(F)F.[CH3:58][O:59][C:60](=[O:105])[NH:61][CH:62]([C:71]([N:73]1[CH2:77][CH2:76][CH2:75][CH:74]1[C:78]1[NH:79][C:80]([C:83]2[CH:88]=[CH:87][C:86]([C:89]3[CH:94]=[CH:93][C:92]([C:95]4[NH:96][C:97]([CH:100]5[CH2:104][CH2:103][CH2:102][NH:101]5)=[N:98][CH:99]=4)=[CH:91][CH:90]=3)=[CH:85][CH:84]=2)=[CH:81][N:82]=1)=[O:72])[CH2:63][CH2:64][O:65][CH2:66][C:67]([F:70])([F:69])[F:68]>>[CH3:55][O:54][C:52](=[O:53])[NH:51][CH:47]([C:46]([N:101]1[CH2:102][CH2:103][CH2:104][CH:100]1[C:97]1[NH:96][C:95]([C:92]2[CH:93]=[CH:94][C:89]([C:86]3[CH:87]=[CH:88][C:83]([C:80]4[NH:79][C:78]([CH:74]5[CH2:75][CH2:76][CH2:77][N:73]5[C:71](=[O:72])[CH:62]([NH:61][C:60]([O:59][CH3:58])=[O:105])[CH2:63][CH2:64][O:65][CH2:66][C:67]([F:70])([F:68])[F:69])=[N:82][CH:81]=4)=[CH:84][CH:85]=3)=[CH:90][CH:91]=2)=[CH:99][N:98]=1)=[O:56])[CH:48]([CH3:50])[CH3:49]

Participants

Reactant 2

HCID 66620507[1-(2-{5-[4'-(2-Pyrrolidin-2-yl-3H-imidazol-4-yl)-biphenyl-4-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carbonyl)-3-(2,2,2-trifluoroethoxy)-propyl]-carbamic acid methyl ester

HCID 66621108(4,4,4-Trifluoro-1-{2-[5-(4'-{2-[1-(2-methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl]-biphenyl-4-yl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-butyl)-carbamic acid methyl ester

Product 1

HCID 66620448[1-(2-{5-[4'-(2-{1-[2-Methoxycarbonylamino-4-(2,2,2-trifluoro-ethoxy)-butyryl]-pyrrolidin-2-yl}-3H-imidazol-4-yl)-biphenyl-4-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-carbamic acid methyl esterYield 45%

Procedure

This compound was made in 45% yield by the same procedure as (4,4,4-Trifluoro-1-{2-[5-(4′-{2-[1-(2-methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-butyl)-carbamic acid methyl ester, using [1-(2-{5-[4′-(2-pyrrolidin-2-yl-3H-imidazol-4-yl)-biphenyl-4-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carbonyl)-3-(2,2,2-trifluoroethoxy)-propyl]-carbamic acid methyl ester as the starting material. LCMS-ESI+: calculated for C41H49F3N8O7: 822.87; observed [M+1]+: 823.45. 1H-NMR: 400 MHz, (CD3OD) δ: 7.82-7.72 (m, 4H), 7.69-7.65 (m, 4H), 7.38-7.32 (m, 2H), 5.22-5.16 (m, 2H), 4.65-4.61 (m, 1H), 4.26-4.21 (m, 1H), 4.04-3.84 (m, 6H), 3.72-3.48 (m, 8H), 2.39-1.98 (m, 10H), 1.88-1.78 (m, 1H), 1.01-0.89 (m, 6H) ppm.

Sources & evidence

ORD record: ord-0aff9c287a9a4a3ab4e880872377f5b2
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822430B2

Reaction notes

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