Reaction SMILES: [C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][CH2:14][CH2:15]OC)[CH2:10][CH:9]1[C:18]1[N:19]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[CH:20]=[C:21]([C:23]2[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][CH:24]=2)[N:22]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].BrCCOC.COC(=O)[NH:46][CH:47]([C:51]([N:53]1CC(OC2C=NC=CN=2)CC1C1NC(C2C=CC(Br)=CC=2)=CN=1)=O)C(C)C.COC(=O)NC(C(N1CC(OCCOC)CC1C1NC(C2C=CC(Br)=CC=2)=CN=1)=O)C(C)C.COC(=O)NC(C(N1C(C2NC(C3C=CC4C(=CC=C(C5C=CC(C6NC(C7CC(OC8C=NC=CN=8)CN7C(=O)C(NC(OC)=O)C(C)C)=NC=6)=CC=5)C=4)C=3)=CN=2)CC2(CC2)C1)=O)C(C)C.COC(=O)NC(C(N1C(C2NC(C3C=CC4C(=CC=C(C5C=CC(C6NC(C7CC(OCCOC)CN7C(=O)C(NC(OC)=O)C(C)C)=NC=6)=CC=5)C=4)C=3)=CN=2)CC2(CC2)C1)=O)C(C)C>>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][C:14]2[CH:15]=[N:53][CH:51]=[CH:47][N:46]=2)[CH2:10][CH:9]1[C:18]1[N:19]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:35])([CH3:36])[CH3:37])[CH:20]=[C:21]([C:23]2[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][CH:24]=2)[N:22]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]
Reactant: COC(=O)NC(C(=O)N1CC(Oc2cnccn2)CC1c1ncc(-c2ccc(Br)cc2)[nH]1)C(C)C
Reactant: COCCOC1CC(c2nc(-c3ccc(Br)cc3)cn2COCC[Si](C)(C)C)N(C(=O)OC(C)(C)C)C1
Agent: COC(=O)NC(C(=O)N1CC(Oc2cnccn2)CC1c1ncc(-c2ccc(-c3ccc4cc(-c5cnc(C6CC7(CC7)CN6C(=O)C(NC(=O)OC)C(C)C)[nH]5)ccc4c3)cc2)[nH]1)C(C)C
Agent: COCCBr
Agent: COCCOC1CC(c2ncc(-c3ccc(-c4ccc5cc(-c6cnc(C7CC8(CC8)CN7C(=O)C(NC(=O)OC)C(C)C)[nH]6)ccc5c4)cc3)[nH]2)N(C(=O)C(NC(=O)OC)C(C)C)C1
Product: CC(C)(C)OC(=O)N1CC(Oc2cnccn2)CC1c1nc(-c2ccc(Br)cc2)cn1COCC[Si](C)(C)C

Procedure:
Title compound was prepared according to the method employed to prepare 2-[4-(4-Bromo-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-4-(2-methoxy-ethoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (Example 1), substituting 2-chloro-pyrazine (50 μl) for 1-bromo-2-methoxy-ethane (94 mg, 40%). {1-[2[5-(4-Bromo-phenyl)-1H-imidazol-2-yl]-4-(pyrazin-2-yloxy)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid methyl ester: Title compound was prepared according to the method employed to prepare {1-[2-[5-(4-Bromo-phenyl)-1H-imidazol-2-yl]-4-(2-methoxy-ethoxy)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid methyl ester (Example 1), substituting 2-[4-(4-Bromo-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-4-(pyrazin-2-yloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (94 mg) for 2-[4-(4-Bromo-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-4-(2-methoxy-ethoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (88 mg, 99%). [1-(6-{5-[6-(4-{2-[1-(2-Methoxycarbonylamino-3-methyl-butyryl)-4-(pyrazin-2-yloxy)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-phenyl)-naphthalen-2-yl]-1H-imidazol-2-yl}-5-aza-spiro[2.4]heptane-5-carbonyl)-2-methyl-propyl]-carbamic acid methyl ester: Title compound was prepared according to the method employed to prepare [1-(6-{5-[6-(4-{2-[1-(2-Methoxycarbonylamino-3-methyl-butyryl)-4-(2-methoxy-ethoxy)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-phenyl)-naphthalen-2-yl]-1H-imidazol-2-yl}-5-aza-spiro[2.4]heptane-5-carbonyl)-2-methyl-propyl]-carbamic acid methyl ester (Example 1), substituting {1-[2[5-(4-Bromo-phenyl)-1H-imidazol-2-yl]-4-(pyrazin-2-yloxy)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid methyl ester (88 mg) for {1-[2[5-(4-Bromo-phenyl)-1H-imidazol-2-yl]-4-(2-methoxy-ethoxy)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid methyl ester (38 mg, 26%). 1H NMR (MeOH-d4, 400 MHz) δ: 8.20-8.10 (m, 3H), 7.90-7.68 (m, 8H), 7.60-7.55 (m. 2H), 7.33-7.30 (m, 2H), 5.68 (m, 1H), 5.39 (m, 1H), 4.44 (m, 1H), 4.04-3.69 (m, 6H), 3.80-3.38 (m, 1H), 3.30 (m, 6H), 2.71 (m, 1H), 2.40-1.90 (m, 5H), 0.90-0.79 (m, 12H), 0.70-0.54 (m, 4H); MS (ESI) m/z 910.5 [M+H]+.