(4S,5R)-2-(6-tert-butyl-4-ethoxy-pyridin-3-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride → HCID 57669933, compound

HRID 1894542Notes

Reaction equation

[C:1]([C:5]1[N:10]=[CH:9][C:8]([C:11]2[N:12]([C:32](Cl)=[O:33])[C@@:13]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)([CH3:24])[C@@:14]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)([CH3:16])[N:15]=2)=[C:7]([O:35][CH2:36][CH3:37])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:38][CH2:39][C@@H:40]1[C@@H:44]([OH:45])[C@@H:43]([OH:46])[CH2:42][N:41]1[CH2:47][CH2:48][OH:49]>>[OH:45][C@H:44]1[C@@H:43]([OH:46])[CH2:42][N:41]([CH2:47][CH2:48][OH:49])[C@@H:40]1[CH2:39][NH:38][C:32]([N:12]1[C@@:13]([C:25]2[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=2)([CH3:24])[C@@:14]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)([CH3:16])[N:15]=[C:11]1[C:8]1[CH:9]=[N:10][C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:6][C:7]=1[O:35][CH2:36][CH3:37])=[O:33]

Participants

Reactant 2

HCID 57669958(4S,5R)-2-(6-tert-butyl-4-ethoxy-pyridin-3-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride

HCID 68933008HCID 68933008, compound

Product 1

HCID 57669933HCID 57669933, compound

Procedure

In a manner analogous to the method described in examples 8, (4S,5R)-2-(6-tert-butyl-4-ethoxy-pyridin-3-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride (example 51) was coupled with (2R,3R,4S)-2-aminomethyl-1-(2-hydroxy-ethyl)-pyrrolidine-3,4-diol (AFID Therapeutics) to give the title compound. HR-MS (ES, m/z) calculated for C36H46Cl2N5O5 [(M+H)+] 698.2871, observed 698.2873.

Sources & evidence

ORD record: ord-6889a8c7cdad4ef69977aec87c87ae71
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513239B2

Reaction notes

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