Ammonia → HCID 59332724, compound

HRID 387282Notes

Reaction equation

HRID 387282 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([OH:13])=O)[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:14]1[CH2:19][CH2:18][S:17](=[O:21])(=[O:20])[C:16]([CH3:23])([CH3:22])[CH2:15]1.O[N:25]1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.N>C(=O)(O)[O-].[Na+].O1CCOCC1.CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH2:25])=[O:13])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:14]1[CH2:19][CH2:18][S:17](=[O:20])(=[O:21])[C:16]([CH3:23])([CH3:22])[CH2:15]1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 59332672HCID 59332672, compound

Product 1

HCID 59332724HCID 59332724, compoundYield 67.9%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
10 °C

Procedure

(racemic)-5-bromo-3-(1,1-dioxido-2,2-dimethylthian-4-yl)-1H-indole-7-carboxylic acid (490 mg, 1.224 mmol), was placed in a microwave flask and dissolved with DMF (2 mL) and 1,4-Dioxane (8 mL). HOBt (1-hydroxybenzotriazole) (165 mg, 1.224 mmol) and EDC (1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide) (657 mg, 3.43 mmol) was added. 0.5N NH3 in dioxane (7.34 mL, 3.67 mmol) was added. The reaction mixture was heated under microwave at 10° C. for 20 minutes. The reaction was diluted with saturated aqueous solution of sodium bicarbonate (20 mL) and extracted with ethyl acetate (2×). The organic layers were combined and washed with water, dried (MgSO4) and the solvent was removed under vacuum. The residue was dissolved in the minimum amount of EtOAc (around 2 mL, sonicating and heating when necessary), precipitated by adding hexane, and then filtering off the solid. This operation was repeated on the filtrate to increase the recovery affording a total of 332 mg of the title compound as a pale yellow powder.

Workup

  1. extractionextracted with ethyl acetate (2×)
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. customthe solvent was removed under vacuum
  5. dissolutionThe residue was dissolved in the minimum amount of EtOAc (around 2 mL, sonicating and heating when necessary)
  6. customprecipitated
  7. additionby adding hexane
  8. filtrationfiltering off the solid
  9. temperatureto increase the recovery

Sources & evidence

ORD record
ord-84b28f1efd194508a619eccc5043b9ce
Source dataset
uspto-grants-2013_02
Patent number
US08372875B2

Reaction notes

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