methyl (S)-1-((S)-2-(5-(4-bromo-3-(difluoromethoxy)phenyl)-1H-imidazol-2-yl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate → HCID 178495681, compound

HRID 1751684Notes

Reaction equation

HRID 1751684 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([C@@H:13]3[CH2:17][CH2:16][CH2:15][N:14]3[C:18](=[O:28])[C@@H:19]([NH:23][C:24](=[O:27])[O:25][CH3:26])[CH:20]([CH3:22])[CH3:21])=[N:10][CH:9]=2)=[CH:4][C:3]=1[O:29][CH:30]([F:32])[F:31].[CH3:33][O:34][CH2:35][C@@H:36]1[CH2:40][N:39]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[C@H:38]([C:48]2[NH:52][C:51]3[C:53]4[C:58]([CH:59]=[CH:60][C:50]=3[N:49]=2)=[CH:57][C:56](B2OC(C)(C)C(C)(C)O2)=[CH:55][CH:54]=4)[CH2:37]1.COC(N[C@@H](C(C)C)C(N1CCC[C@H]1C1NC2C3C(C=CC=2N=1)=CC(C1C=C2C(=CC=1)C1NC([C@@H]4C[C@H](COC)CN4C(=O)[C@@H](NC(=O)OC)C(C)C)=NC=1C=C2)=CC=3)=O)=O>>[F:31][CH:30]([F:32])[O:29][C:3]1[CH:4]=[C:5]([C:8]2[NH:12][C:11]([C@@H:13]3[CH2:17][CH2:16][CH2:15][N:14]3[C:18](=[O:28])[C@@H:19]([NH:23][C:24]([O:25][CH3:26])=[O:27])[CH:20]([CH3:22])[CH3:21])=[N:10][CH:9]=2)[CH:6]=[CH:7][C:2]=1[C:56]1[CH:57]=[C:58]2[C:53](=[CH:54][CH:55]=1)[C:51]1[NH:52][C:48]([C@@H:38]3[CH2:37][C@H:36]([CH2:35][O:34][CH3:33])[CH2:40][N:39]3[C:41]([O:43][C:44]([CH3:47])([CH3:45])[CH3:46])=[O:42])=[N:49][C:50]=1[CH:60]=[CH:59]2

Participants

4

Reactant 3

HCID 86708803methyl (S)-1-((S)-2-(5-(4-bromo-3-(difluoromethoxy)phenyl)-1H-imidazol-2-yl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamateHCID 178495668HCID 178495668, compoundHCID 178495671HCID 178495671, compound

Product 1

HCID 178495681HCID 178495681, compound

Procedure

(2S,4S)-tert-Butyl 2-(7-(2-(difluoromethoxy)-4-(2-((S)-1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)pyrrolidin-2-yl)-1H-imidazol-5-yl)phenyl)-1H-naphtho[1,2-d]imidazol-2-yl)-4-(methoxymethyl)pyrrolidine-1-carboxylate was prepared from methyl (S)-1-((S)-2-(5-(4-bromo-3-(difluoromethoxy)phenyl)-1H-imidazol-2-yl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate and (2S,4S)-tert-butyl 4-(methoxymethyl)-2-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-naphtho[1,2-d]imidazol-2-yl)pyrrolidine-1-carboxylate using the same conditions employed in the synthesis of methyl {(2S)-1-[(2S,4S)-2-{2′-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}pyrrolidin-2-yl]-1H,1′H-7,7′-binaphtho[1,2-d]imidazol-2-yl}-4-(methoxymethyl)pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}carbamate.

Sources & evidence

ORD record
ord-95da6f18dbc44d319881d510b1124f33
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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