1-Hydroxybenzotriazole → HCID 66726121, compound

HRID 1042197Notes

Reaction equation

HRID 1042197 reaction equation
O1CCCC1.[CH2:6]([NH2:8])[CH3:7].[CH2:9]([C:11]1[CH:12]=[C:13]([O:29][C:30]2[CH:31]=[N:32][C:33]([S:36]([CH3:39])(=[O:38])=[O:37])=[CH:34][CH:35]=2)[CH:14]=[C:15]2[C:19]=1[NH:18][C:17]([C:20]1[S:21][CH:22]([CH2:25][C:26](O)=[O:27])[CH2:23][N:24]=1)=[CH:16]2)[CH3:10].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>O.CN(C)C=O>[CH2:6]([NH:8][C:26](=[O:27])[CH2:25][CH:22]1[S:21][C:20]([C:17]2[NH:18][C:19]3[C:15]([CH:16]=2)=[CH:14][C:13]([O:29][C:30]2[CH:31]=[N:32][C:33]([S:36]([CH3:39])(=[O:38])=[O:37])=[CH:34][CH:35]=2)=[CH:12][C:11]=3[CH2:9][CH3:10])=[N:24][CH2:23]1)[CH3:7]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58081018HCID 58081018, compoundHCID 66726184Ethylamine tetrahydrofuran

Product 1

HCID 66726121HCID 66726121, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixed solution of 2.0M-ethylamine tetrahydrofuran solution (0.33 mL), [2-(7-ethyl-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indol-2-yl)-4,5-dihydro-1,3-thiazol-5-yl]acetic acid (200 mg), and N,N-dimethylformamide (10 mL) were added 1-hydroxybenzotriazole (89 mg), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (125 mg) under ice-cooling, and the mixture was stirred under ice-cooling and then at room temperature for 15 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:methanol=100:0 to 90:10, volume ratio), and the obtained pale-yellow oil was recrystallized from ethyl acetate-hexane to give the title compound (92 mg, yield 44%) as colorless crystals.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with aqueous sodium hydrogen carbonate solution and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customthe obtained pale-yellow oil was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-798895ee59514accab854e668e6f5d88
Source dataset
uspto-grants-2013_10
Patent number
US08557805B2

Reaction notes

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