2-{4-[4-(4,4,5,5-Tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl]-1h-imidazol-2-yl}pyrrolidine-1-carboxylic acid tert-butyl ester → (1-{2-[6-(4-{2-[2-(2-Methoxycarbonylamino-3-methyl-butyryl)-2-aza-bicyclo[2.2.1]hept-3-yl]-3H-imidazol-4-yl}-phenyl)-1H-benzoimidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester

HRID 2038932Notes

Reaction equation

HRID 2038932 reaction equation
[CH3:1][O:2][C:3](=[O:38])[NH:4][CH:5]([C:9]([N:11]1[CH:16]([C:17]2[NH:18][C:19]([C:22]3[CH:27]=[CH:26][C:25](B4OC(C)(C)C(C)(C)O4)=[CH:24][CH:23]=3)=[CH:20][N:21]=2)[CH:15]2[CH2:37][CH:12]1[CH2:13][CH2:14]2)=[O:10])[CH:6]([CH3:8])[CH3:7].[CH3:39][O:40][C:41](=[O:63])[NH:42][CH:43]([C:46]([N:48]1[CH2:52][CH2:51][CH2:50][CH:49]1[C:53]1[NH:57][C:56]2[CH:58]=[C:59](Br)[CH:60]=[CH:61][C:55]=2[N:54]=1)=[O:47])[CH2:44][CH3:45].[C:64](OC(N1CCCC1C1NC(C2C=CC(B3OC(C)(C)C(C)(C)O3)=CC=2)=CN=1)=O)(C)(C)C.C(OC(N1CCC(C2NC(C3C=CC(Br)=CC=3)=CN=2)C1)=O)(C)(C)C>>[CH3:39][O:40][C:41](=[O:63])[NH:42][CH:43]([C:46]([N:48]1[CH2:52][CH2:51][CH2:50][CH:49]1[C:53]1[NH:57][C:56]2[CH:58]=[C:59]([C:25]3[CH:24]=[CH:23][C:22]([C:19]4[NH:18][C:17]([CH:16]5[CH:15]6[CH2:37][CH:12]([CH2:13][CH2:14]6)[N:11]5[C:9](=[O:10])[CH:5]([NH:4][C:3]([O:2][CH3:1])=[O:38])[CH:6]([CH3:8])[CH3:7])=[N:21][CH:20]=4)=[CH:27][CH:26]=3)[CH:60]=[CH:61][C:55]=2[N:54]=1)=[O:47])[CH:44]([CH3:64])[CH3:45]

Participants

5

Reactant 4

HCID 574497592-{4-[4-(4,4,5,5-Tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl]-1h-imidazol-2-yl}pyrrolidine-1-carboxylic acid tert-butyl esterHCID 59611262tert-Butyl 3-(5-(4-bromophenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylateHCID 66620297[2-methyl-1-(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-carbonyl)-propyl]-carbamic acid methyl esterHCID 66620886{1-[2-(6-bromo-1H-benzoimidazol-2-yl)-pyrrolidine-1-carbonyl]-propyl}-carbamic acid methyl ester

Product 1

HCID 66620950(1-{2-[6-(4-{2-[2-(2-Methoxycarbonylamino-3-methyl-butyryl)-2-aza-bicyclo[2.2.1]hept-3-yl]-3H-imidazol-4-yl}-phenyl)-1H-benzoimidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester

Procedure

Following the procedure used to prepare compound 2-(5-{4′-[2-(1-Boc-pyrrolidin-3-yl)-3H-imidazol-4-yl}-biphenyl-4-yl]-11′-imidazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester, except that [2-methyl-1-(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-carbonyl)-propyl]-carbamic acid methyl ester and {1-[2-(6-bromo-1H-benzoimidazol-2-yl)-pyrrolidine-1-carbonyl]-propyl}-carbamic acid methyl ester were used instead of 2-{5-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester and 3-[5-(4-bromo-phenyl)-1H-imidazol-2-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester. 1H-NMR (300 MHz, CD3OD) δ 8.10-7.80 (m, 7H), 5.42-5.30 (m, 1H), 4.65 (s, 1H), 4.40-4.25 (m, 2H), 4.20-3.90 (m, 2H, 3.80-3.60 (m, 6H), 3.00-2.80 (m, 1H), 2.70-2.55 (m, 1H), 2.50-1.60 (m, 12H), 1.10-0.80 (m, 12H); m/z 739.3 (M+H)+.

Sources & evidence

ORD record
ord-3ae8dcc06e054255b42f82035e380a44
Source dataset
uspto-grants-2013_11
Patent number
US08575118B2

Reaction notes

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