Chloride → HCID 68683466, compound

HRID 2264036Notes

Reaction equation

HRID 2264036 reaction equation
C1(C2C=CC(C(Cl)=O)=C(OCC)C=2)CC1.BrC1C=CC(C(O)=O)=C(O)C=1.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:46]([C:57]3[CH:62]=[CH:61][C:60]([C:63](C)([CH3:65])[CH3:64])=[CH:59][C:58]=3[O:67][CH2:68][CH3:69])=[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:55]=[CH:54][C:53]([Cl:56])=[CH:52][CH:51]=3)([CH3:49])[NH:47][C:46]([C:57]3[CH:62]=[CH:61][C:60]([CH:63]4[CH2:65][CH2:64]4)=[CH:59][C:58]=3[O:67][CH2:68][CH3:69])=[N:45]2)=[CH:40][CH:39]=1

Participants

7

Reactant 6

HCID 312ChlorideHCID 6340IodoethaneHCID 2687374-Bromo-2-hydroxybenzoic acidHCID 2760897Cyclopropylboronic acidHCID 53628801rac-(4S*,5R*)-2-(4-tert-butyl-2-ethoxy-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-1H-imidazoleHCID 86612889HCID 86612889, compound

Product 1

HCID 68683466HCID 68683466, compound

Procedure

rac-(4S*,5R*)-4,5-Bis-(4-chloro-phenyl)-2-(4-cyclopropyl-2-ethoxy-phenyl)-4,5-dimethyl-4,5-dihydro-1H-imidazole was prepared from 4-cyclopropyl-2-ethoxy-benzoyl chloride (prepared from 4-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-e92efc4d7cbd4c3ea25452644ea96cd8
Source dataset
uspto-grants-2010_12
Patent number
US07851626B2

Reaction notes

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