HCID 18461400, compound → HCID 86758432, compound

HRID 2303783Notes

Reaction equation

HRID 2303783 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:46]=[CH:45][C:12]([O:13][CH2:14][C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]4[CH:30]=[CH:29][C:28]([N:31]5[CH:35]=[CH:34][N:33]=[CH:32]5)=[CH:27][CH:26]=4)=[CH:20][C:19]=3[N:36]([CH3:44])C(=O)OC(C)(C)C)=O)=[CH:11][CH:10]=2)[S:3]1.[ClH:47].O1CCOCC1>>[ClH:47].[ClH:47].[N:31]1([C:28]2[CH:29]=[CH:30][C:25]([O:24][C:21]3[CH:22]=[CH:23][C:18]4[N:17]=[C:15]([CH2:14][O:13][C:12]5[CH:45]=[CH:46][C:9]([CH2:8][CH:4]6[S:3][C:2](=[O:1])[NH:6][C:5]6=[O:7])=[CH:10][CH:11]=5)[N:36]([CH3:44])[C:19]=4[CH:20]=3)=[CH:26][CH:27]=2)[CH:35]=[CH:34][N:33]=[CH:32]1

Participants

3

Reactant 2

HCID 18461400HCID 18461400, compoundHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 86758432HCID 86758432, compound

Procedure

A mixture of t-butyl N-{2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxyacetylamino]-5-[4-(imidazole-1-yl)phenoxy]phenyl}-N-methylcarbamate (1.75 g) and 4N hydrogen chloride/dioxane (20 ml) was stirred at ambient temperature for 19 hours. The solvent of the reaction mixture was evaporated to dryness. To the residue was added ethyl acetate and insoluble product was collected by filtration. The product was purified by reversed-phase high performance liquid chromatography using acetonitrile/water=7/13 as the eluant and was treated with 4N hydrogen chloride/acetate to give the title compound (0.20 g).

Workup

  1. customThe solvent of the reaction mixture was evaporated to dryness
  2. additionTo the residue was added ethyl acetate and insoluble product
  3. filtrationwas collected by filtration
  4. customThe product was purified by reversed-phase high performance liquid chromatography
  5. additionwas treated with 4N hydrogen chloride/acetate

Sources & evidence

ORD record
ord-e7ea5a9b17604419b70bffd141140dde
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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