2-[5-(4-{3-[2-(1-Boc-pyrrolidin-2-yl)-3H-imidazol-4-yl]-phenoxy}-phenyl)-1H-imidazol-2-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester → [1-(2-{5-[4-(3-{2-[1-(2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-phenoxy)-phenyl]-1H-imidazol-2-yl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-carbamic acid methyl ester

HRID 79634Notes

Reaction equation

COC(=O)NC(C(N1CCC(C2NC(C3C=CC([C:27]4[CH:32]=[CH:31][C:30]([C:33]5[NH:34][C:35]([CH:38]6[CH2:42][CH2:41][CH2:40][N:39]6[C:43](=[O:53])[CH:44]([NH:48][C:49]([O:51][CH3:52])=[O:50])[CH:45]([CH3:47])[CH3:46])=[N:36][CH:37]=5)=[CH:29][CH:28]=4)=CC=3)=CN=2)C1)=O)C(C)C.C(O[C:60]([N:62]1[CH2:66][CH2:65][CH2:64][CH:63]1[C:67]1[NH:68][C:69]([C:72]2[CH:77]=[CH:76][C:75]([O:78]C3C=CC=C(C4NC(C5CCCN5C(OC(C)(C)C)=O)=NC=4)C=3)=[CH:74][CH:73]=2)=[CH:70][N:71]=1)=[O:61])(C)(C)C>>[CH3:52][O:51][C:49](=[O:50])[NH:48][CH:44]([C:60]([N:62]1[CH2:66][CH2:65][CH2:64][CH:63]1[C:67]1[NH:68][C:69]([C:72]2[CH:77]=[CH:76][C:75]([O:78][C:28]3[CH:27]=[CH:32][CH:31]=[C:30]([C:33]4[NH:34][C:35]([CH:38]5[CH2:42][CH2:41][CH2:40][N:39]5[C:43](=[O:53])[CH:44]([NH:48][C:49]([O:51][CH3:52])=[O:50])[CH:45]([CH3:46])[CH3:47])=[N:36][CH:37]=4)[CH:29]=3)=[CH:74][CH:73]=2)=[CH:70][N:71]=1)=[O:61])[CH:45]([CH3:47])[CH3:46]

Participants

Reactant 2

HCID 666202152-[5-(4-{3-[2-(1-Boc-pyrrolidin-2-yl)-3H-imidazol-4-yl]-phenoxy}-phenyl)-1H-imidazol-2-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester

HCID 66620702(1-{3-[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]-2-methyl-propyl)-carbamic acid methyl ester

Product 1

HCID 66621096[1-(2-{5-[4-(3-{2-[1-(2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-phenoxy)-phenyl]-1H-imidazol-2-yl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-carbamic acid methyl ester

Procedure

Following the procedure used to prepare compound (1-{3-[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}-2-methyl-propyl)-carbamic acid methyl ester, except that 2-[5-(4-{3-[2-(1-Boc-pyrrolidin-2-yl)-3H-imidazol-4-yl]-phenoxy}-phenyl)-1H-imidazol-2-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester was used instead of 2-(5-{4′-[2-(1-Boc-pyrrolidin-3-yl)-3H-imidazol-4-yl]-biphenyl-4-yl}-1H-imidazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester. 1H-NMR (300 MHz, CD3OD) δ 7.80-7.10 (m, 10H), 5.30-5.15 (m, 2H), 4.30-4.20 (m, 2H), 4.18-4.05 (m, 2H), 3.95-3.80 (m, 2H), 3.70-3.60 (m, 6H), 2.65-2.45 (m, 2H), 2.40-2.00 (m, 8H), 1.05-0.85 (m, 12H); m/z 755.3 (M+H)+.

Sources & evidence

ORD record: ord-fc8bff580e094ca78aba6127d104f110
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841278B2

Reaction notes

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