1-Hydroxybenzotriazole → HCID 58236936, compound

HRID 1188951Notes

Reaction equation

HRID 1188951 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([O:14][C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=2)[CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11](O)=[O:12])=[CH:7]2.[CH2:25]([S:32][CH:33]([CH:36]([O:39][CH3:40])[O:37][CH3:38])[CH2:34][NH2:35])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O>[CH2:25]([S:32][CH:33]([CH:36]([O:37][CH3:38])[O:39][CH3:40])[CH2:34][NH:35][C:11]([C:8]1[NH:9][C:10]2[C:6]([CH:7]=1)=[CH:5][C:4]([O:14][C:15]1[CH:16]=[CH:17][C:18]([S:21]([CH3:24])(=[O:22])=[O:23])=[CH:19][CH:20]=1)=[CH:3][C:2]=2[OH:1])=[O:12])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 574759902-(Benzylthio)-3,3-dimethoxypropan-1-amineHCID 58237102HCID 58237102, compound

Product 1

HCID 58236936HCID 58236936, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ice-cooled and stirred mixture of 7-hydroxy-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylic acid (2.1 g) and 2-(benzylsulfanyl)-3,3-dimethoxypropan-1-amine (2.9 g) in N,N-dimethylformamide (50 mL) were added 1-hydroxybenzotriazole (1.1 g), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.6 g). After stirred at 4° C. to room temperature for 15 h, the reaction mixture was concentrated in vacuo and the residue was purified by silica gel chromatography (ethyl acetate:hexane=35:65 to 60:40, volume ratio) to give light yellow crystals, which were washed with ethyl acetate-hexane to give the title compound (1.73 g, 50%) as pale yellow needles. MS 569 (MH+).

Workup

  1. stirringAfter stirred at 4° C. to room temperature for 15 h
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customthe residue was purified by silica gel chromatography (ethyl acetate:hexane=35:65 to 60:40, volume ratio)
  4. customto give light yellow crystals, which
  5. washwere washed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-d1b6df01d1b94c8d8abdc321b24a0293
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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