Diisopropylethylamine → HCID 57809249, compound

HRID 2105878Notes

Reaction equation

HRID 2105878 reaction equation
[Cl:1][C:2]1[C:7]([S:8](=[O:12])(=[O:11])[NH:9][CH3:10])=[CH:6][C:5]([C:13]2[N:14]([C:32](Cl)=[O:33])[CH:15]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)[CH:16]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[N:17]=2)=[C:4]([O:35][CH2:36][CH3:37])[CH:3]=1.O.[OH:39][N:40]1[C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=2[N:42]=[N:41]1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[N:40]1([O:39][C:32]([N:14]2[C@H:15]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)[C@H:16]([C:18]3[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=3)[N:17]=[C:13]2[C:5]2[CH:6]=[C:7]([S:8](=[O:12])(=[O:11])[NH:9][CH3:10])[C:2]([Cl:1])=[CH:3][C:4]=2[O:35][CH2:36][CH3:37])=[O:33])[C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=2[N:42]=[N:41]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 86607798HCID 86607798, compound

Product 1

HCID 57809249HCID 57809249, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In an analogous manner as described in example 29, 5-[4,5-bis-(4-chloro-phenyl)-4,5-dihydro-1H-imidazol-2-yl]-2-chloro-4-ethoxy-N-methyl-benzenesulfonamide was treated with phosgene and diisopropylethylamine in methylene chloride to give 2-(4-chloro-2-ethoxy-5-methylsulfamoyl-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dihydro-imidazole-1-carbonyl chloride. The crude carbamoyl chloride was then reacted with 1-hydroxybenzotriazole hydrate and diisopropylethylamine in methylene chloride to give the racemic 2-(4-chloro-2-ethoxy-5-methylsulfamoyl-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dihydro-imidazole-1-carboxylic acid benzotriazol-1-yl ester after purification by flash column chromatography (silica gel, eluting with a gradient of ethyl acetate in hexanes).

Sources & evidence

ORD record
ord-33f932058f9845b2a97fc35c175bf47d
Source dataset
uspto-grants-2009_08
Patent number
US07579368B2

Reaction notes

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