Hydrochloric Acid → 1-(2,6-Diisopropylphenyl)-3-[2-(4-[2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]phenyl)ethyl]urea hydrochloride

HRID 412348

Reaction equation

HRID 412348 reaction equation
[ClH:1].Cl.[NH2:3][CH2:4][CH2:5][C:6]1[CH:38]=[CH:37][C:9]([O:10][C:11]2[CH:12]=[CH:13][C:14]3[N:18]=[C:17]([CH2:19][O:20][C:21]4[CH:34]=[CH:33][C:24]([CH2:25][CH:26]5[S:30][C:29](=[O:31])[NH:28][C:27]5=[O:32])=[CH:23][CH:22]=4)[N:16]([CH3:35])[C:15]=3[CH:36]=2)=[CH:8][CH:7]=1.[CH:39]([C:42]1[CH:47]=[CH:46][CH:45]=[C:44]([CH:48]([CH3:50])[CH3:49])[C:43]=1[N:51]=[C:52]=[O:53])([CH3:41])[CH3:40].C(N(CC)C(C)C)(C)C.Cl>O1CCCC1.C(OCC)(=O)C.C(OCC)C.CN(C)C=O>[ClH:1].[CH:39]([C:42]1[CH:47]=[CH:46][CH:45]=[C:44]([CH:48]([CH3:49])[CH3:50])[C:43]=1[NH:51][C:52]([NH:3][CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:10][C:11]2[CH:12]=[CH:13][C:14]3[N:18]=[C:17]([CH2:19][O:20][C:21]4[CH:34]=[CH:33][C:24]([CH2:25][CH:26]5[S:30][C:29](=[O:31])[NH:28][C:27]5=[O:32])=[CH:23][CH:22]=4)[N:16]([CH3:35])[C:15]=3[CH:36]=2)=[CH:37][CH:38]=1)=[O:53])([CH3:40])[CH3:41]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 922592,6-Diisopropylphenyl isocyanateHCID 865877735-[4-[6-[4-(2-aminoethyl)phenoxy]-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride

Product 1

HCID 185376291-(2,6-Diisopropylphenyl)-3-[2-(4-[2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]phenyl)ethyl]urea hydrochlorideYield 78.2%

Reagents, catalysts & solvents 4

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(2,6-Diisopropylphenyl)-3-[2-(4-[2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]phenyl)ethyl]urea was obtained by a similar procedure to that described in Example 31 using 5-[4-[6-[4-(2-aminoethyl)phenoxy]-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride (0.4 g), 2,6-diisopropylphenyl isocyanate (0.14 g), N,N-diisopropylethylamine (0.18 g) and anhydrous N,N-dimethylformamide (15 ml). To a solution of the product in tetrahydrofuran (10 ml) was added 4N hydrogen chloride in ethyl acetate (5 ml) and the mixture was stirred at room temperature for 1.5 hours. To the reaction mixture was added diethyl ether (15 ml) and this mixture was stirred for 1 hour. The precipitate was isolated by filtration and washed with ethyl acetate and n-hexane to afford the title compound (0.4 g, mp 153-155° C.).

Workup

  1. stirringthis mixture was stirred for 1 hour
  2. customThe precipitate was isolated by filtration
  3. washwashed with ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-b90e51eda6b940ce8c9eb858b4901471
Source dataset
uspto-grants-2003_05
Patent number
US06562849B1

Linked notes

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