1-Hydroxybenzotriazole → HCID 22627517, compound

HRID 278109Notes

Reaction equation

HRID 278109 reaction equation
[OH:1][N:2]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[Cl:23][C:24]1[CH:50]=[CH:49][CH:48]=[CH:47][C:25]=1[CH2:26][N:27]1[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([C:36](O)=[O:37])[CH:34]=2)[C:29]([C:39](=[O:43])[CH:40]([CH3:42])[CH3:41])=[C:28]1[CH2:44][CH2:45][CH3:46].Cl.NO.C(N(C(C)C)CC)(C)C>CN(C)C=O>[Cl:23][C:24]1[CH:50]=[CH:49][CH:48]=[CH:47][C:25]=1[CH2:26][N:27]1[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([C:36]([NH:2][OH:1])=[O:37])[CH:34]=2)[C:29]([C:39](=[O:43])[CH:40]([CH3:42])[CH3:41])=[C:28]1[CH2:44][CH2:45][CH3:46]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22627188HCID 22627188, compound

Product 1

HCID 22627517HCID 22627517, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

1-Hydroxybenzotriazole (68 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (72 mg) were added to a solution of 1-(2-chlorobenzyl)-3-isobutyryl-2-propylindole-6-carboxylic acid (100 mg) in dimethylformamide (3 ml), and the mixture was stirred at 20° C. overnight, then hydroxylamine hydrochloride (35 mg) and diisopropylethylamine (0.088 ml) were added. After stirred at 20° C. for 2 hours, the reaction mixture was partitioned between ethyl acetate and water. The organic phase was washed with 1N hydrochloric acid and brine, dried over sodium sulfate, and evaporated in vacuo. The residue was purified by preparative thin layer chromatography with 10% methanol in chloroform and recrystallization from ethyl acetate to give 1-(2-chlorobenzyl)-3-isobutyryl-2-propylindole-6-carbohydroxamic acid (67 mg) as pale red crystals.

Workup

  1. stirringAfter stirred at 20° C. for 2 hours
  2. customthe reaction mixture was partitioned between ethyl acetate and water
  3. washThe organic phase was washed with 1N hydrochloric acid and brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by preparative thin layer chromatography with 10% methanol in chloroform and recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-46658548518740fa98d180e1caca7c58
Source dataset
uspto-grants-2002_03
Patent number
US06358992B1

Reaction notes

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