4-Fluorophenyl isocyanate → 1-(4-[2-[4-(2,4-Dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]phenyl)-1-n-hexyl-3-(4-fluorophenyl)urea

HRID 412336Notes

Reaction equation

HRID 412336 reaction equation
[CH2:1]([NH:7][C:8]1[CH:40]=[CH:39][C:11]([O:12][C:13]2[CH:14]=[CH:15][C:16]3[N:20]=[C:19]([CH2:21][O:22][C:23]4[CH:36]=[CH:35][C:26]([CH2:27][CH:28]5[S:32][C:31](=[O:33])[NH:30][C:29]5=[O:34])=[CH:25][CH:24]=4)[N:18]([CH3:37])[C:17]=3[CH:38]=2)=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[F:41][C:42]1[CH:47]=[CH:46][C:45]([N:48]=[C:49]=[O:50])=[CH:44][CH:43]=1>O1CCCC1>[O:33]=[C:31]1[NH:30][C:29](=[O:34])[CH:28]([CH2:27][C:26]2[CH:35]=[CH:36][C:23]([O:22][CH2:21][C:19]3[N:18]([CH3:37])[C:17]4[CH:38]=[C:13]([O:12][C:11]5[CH:39]=[CH:40][C:8]([N:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:49]([NH:48][C:45]6[CH:46]=[CH:47][C:42]([F:41])=[CH:43][CH:44]=6)=[O:50])=[CH:9][CH:10]=5)[CH:14]=[CH:15][C:16]=4[N:20]=3)=[CH:24][CH:25]=2)[S:32]1

Participants

4

Reactant 2

HCID 709554-Fluorophenyl isocyanateHCID 865877705-[4-[6-(4-n-Hexylaminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4dione

Product 1

HCID 101689401-(4-[2-[4-(2,4-Dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]phenyl)-1-n-hexyl-3-(4-fluorophenyl)urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-[4-[6-(4-n-hexylaminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione (0.39 g), 4-fluorophenyl isocyanate (0.11 g) and anhydrous tetrahydrofuran (20 ml) was allowed to stand at room temperature for 2 days. The reaction mixture was concentrated and partitioned between ethyl acetate and water. The extract was dried over anhydrous sodium sulfate and then concentrated. The residue was chromatographed on a silica gel column using ethyl acetate:n-hexane=3:2 as the eluant and the product was reprecipitated from a mixture of ethyl acetate and diisopropyl ether to afford the title compound (0.32 g, Rf=0.45: thin layer chromatography on a silica gel plate using ethyl acetate:n-hexane=2:1 as the eluant).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between ethyl acetate and water
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was chromatographed on a silica gel column
  6. customn-hexane=3:2 as the eluant and the product was reprecipitated from a mixture of ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-32eaf8a7b1ec4f5680a8d31649540da9
Source dataset
uspto-grants-2003_05
Patent number
US06562849B1

Reaction notes

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