Chloride → HCID 68682249, compound

HRID 2264037Notes

Reaction equation

[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([O:13][CH2:14][CH3:15])=[C:8]([CH:12]=2)[C:9](Cl)=O)[CH2:3][CH2:2]1.BrC1C=CC(O)=C(C=1)C(O)=O.ICC.C1(B(O)O)CC1.[Cl-].[Cl:37][C:38]1[CH:43]=[CH:42][C:41]([C:44]2([CH3:70])[C:48]([C:50]3[CH:55]=[CH:54][C:53]([Cl:56])=[CH:52][CH:51]=3)([CH3:49])[NH:47]C(C3C=CC(C(C)(C)C)=CC=3OCC)=[N:45]2)=[CH:40][CH:39]=1>>[Cl:37][C:38]1[CH:43]=[CH:42][C:41]([C:44]2([CH3:70])[C:48]([C:50]3[CH:51]=[CH:52][C:53]([Cl:56])=[CH:54][CH:55]=3)([CH3:49])[NH:47][C:9]([C:8]3[CH:12]=[C:4]([CH:1]4[CH2:3][CH2:2]4)[CH:5]=[CH:6][C:7]=3[O:13][CH2:14][CH3:15])=[N:45]2)=[CH:40][CH:39]=1

Participants

Reactant 6

HCID 312Chloride

HCID 6340Iodoethane

HCID 69725-Bromosalicylic acid

HCID 2760897Cyclopropylboronic acid

HCID 53628801rac-(4S*,5R*)-2-(4-tert-butyl-2-ethoxy-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-1H-imidazole

HCID 86612890HCID 86612890, compound

Product 1

HCID 68682249HCID 68682249, compound

Procedure

rac-(4S*,5R*)-4,5-Bis-(4-chloro-phenyl)-2-(5-cyclopropyl-2-ethoxy-phenyl)-4,5-dimethyl-4,5-dihydro-1H-imidazole was prepared from 5-cyclopropyl-2-ethoxy-benzoyl chloride (prepared from 5-bromo-2-hydroxy-benzoic acid by alkylation with iodoethane, Suzuki coupling with cyclopropyl boronic acid, then saponification and conversion to the chloride) and meso-2,3-bis-(4-chlorophenyl)-2,3-butanediamine (example 1) in an analogous manner as described in example 2 (method 1).

Sources & evidence

ORD record: ord-57ac322d950341e1be43359bfd8c4c38
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851626B2

Reaction notes

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