1-Isocyanatoadamantane → HCID 18537598, compound

HRID 412357

Reaction equation

HRID 412357 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([O:12][C:13]1[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]=1)[CH:8]=[CH:7]2.[C:39]12([N:49]=[C:50]=[O:51])[CH2:48][CH:43]3[CH2:44][CH:45]([CH2:47][CH:41]([CH2:42]3)[CH2:40]1)[CH2:46]2>CN(C)C=O>[C:39]12([NH:49][C:50]([NH:1][C:2]3[C:11]4[C:6](=[CH:7][CH:8]=[C:9]([O:12][C:13]5[CH:14]=[CH:15][C:16]6[N:20]=[C:19]([CH2:21][O:22][C:23]7[CH:24]=[CH:25][C:26]([CH2:27][CH:28]8[S:32][C:31](=[O:33])[NH:30][C:29]8=[O:34])=[CH:35][CH:36]=7)[N:18]([CH3:37])[C:17]=6[CH:38]=5)[CH:10]=4)[CH:5]=[CH:4][CH:3]=3)=[O:51])[CH2:48][CH:43]3[CH2:44][CH:45]([CH2:47][CH:41]([CH2:42]3)[CH2:40]1)[CH2:46]2

Participants

4

Reactant 2

HCID 20599951-IsocyanatoadamantaneHCID 98327115-[4-[6-(8-aminonaphthalen-2-yloxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione

Product 1

HCID 18537598HCID 18537598, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-[4-[6-(8-aminonaphthalen-2-yloxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione (0.5 g) in anhydrous N,N-dimethylformamide (10 ml) was added 1-adamantyl isocyanate (0.18 g) and the mixture was stirred at room temperature for 5 days. The reaction mixture was concentrated. The residue was purified by preparative reverse phase high performance liquid chromatography using acetonitrile:water=50:50→60:40→70:30 as the eluant to afford the title compound (0.45 g, mp 250° C. (dec)).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe residue was purified by preparative reverse phase high performance liquid chromatography

Sources & evidence

ORD record
ord-2ce4ac67b7434aaabd7e58cbb1a85ba7
Source dataset
uspto-grants-2003_05
Patent number
US06562849B1

Linked notes

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