Tert-Butylamine → HCID 9794393, compound

HRID 650115Notes

Reaction equation

HRID 650115 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C(N(CC)CC)C.CS(Cl)(=O)=O.[C:25]([NH2:29])([CH3:28])([CH3:27])[CH3:26]>CN(C=O)C.O.[Cl-].[Na+]>[C:25]([NH:29][C:10]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][CH:2]=[CH:3]2)=[O:12])([CH3:28])([CH3:27])[CH3:26]

Participants

8

Reactant 4

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 742801H-Indole-5-Carboxylic Acid

Product 1

HCID 9794393HCID 9794393, compoundYield 28%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 5234Sodium ChlorideSolventHCID 6228DimethylformamideSolvent

Procedure

To a cooled to −30° C. solution of indole-5-carboxylic acid and triethylamine in DMF was added methyl sulfonyl chloride in portions to avoid temperature elevation. Following the addition, solution was warmed to room temperature and was stirred for 1 hour and 15 minutes. Reaction mixture was then cooled to −20° C. and N-tert-butyl-amine was added in two portions so the temperature remained at −10° C. After 13 hours of stirring, the solution was diluted with water and saturated with sodium chloride. The solution was extracted with ethyl acetate and the organic phase was dried over magnesium sulfate, filtered and concentrated under vacuum to afford the title compound as a thick brown oil (NMR showed 34% DMF) (28% yield), melting point=176.4° C.

Workup

  1. additionthe addition, solution
  2. customReaction mixture
  3. temperaturewas then cooled to −20° C.
  4. customremained at −10° C
  5. stirringAfter 13 hours of stirring
  6. extractionThe solution was extracted with ethyl acetate
  7. dry with materialthe organic phase was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3bbd5f5d70e8467f97ebf8263e0e9abd
Source dataset
uspto-grants-2001_08
Patent number
US06271265B1

Reaction notes

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