Hydrochloric Acid → HCID 44236213, compound

HRID 549406Notes

Reaction equation

HRID 549406 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][C:17]=2[CH3:25])[CH:10]([C:26]2[CH:31]=[CH:30][C:29](/[CH:32]=[CH:33]/[C:34](=[O:37])[NH:35][OH:36])=[CH:28][CH:27]=2)[CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[OH:36][NH:35][C:34](=[O:37])/[CH:33]=[CH:32]/[C:29]1[CH:28]=[CH:27][C:26]([CH:10]2[CH2:9][NH:8][CH2:13][CH2:12][N:11]2[CH2:14][CH2:15][C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][C:17]=2[CH3:25])=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57899228HCID 57899228, compound

Product 1

HCID 44236213HCID 44236213, compoundYield 109.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 3-[4-((E)-2-hydroxycarbamoyl-vinyl)-phenyl]-4-[2-(2-methyl-1H-indol-3-yl)-ethyl]-piperazine-1-carboxylic acid tert-butyl ester (55.8 mg, 0.111 mmol) in dioxane (5 mL) was treated with a solution of hydrochloric acid in dioxane (0.03 mL, 4 M) and the resulting mixture was stirred at room temperature. A brown precipitate was collected and dissolved in water. The aqueous solution was washed with diethyl ether and concentrated to give (E)-N-hydroxy-3-(4-{1-[2-(2-methyl-1H-indol-3-yl)-ethyl]-piperazin-2-yl}-phenyl)-acrylamide (89, 49 mg, 99% yield). LCMS (m/z): 405.1 (M+1).

Workup

  1. customA brown precipitate was collected
  2. dissolutiondissolved in water
  3. washThe aqueous solution was washed with diethyl ether
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-df560ff21fcd468984271c73e2310422
Source dataset
uspto-grants-2011_05
Patent number
US07943652B2

Reaction notes

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