Hydrochloric Acid → HCID 23573454, compound

HRID 1824993Notes

Reaction equation

HRID 1824993 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:6]([C:19]([NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:20])=[CH:5]2.C(N(CC)CC)C.[CH3:35][C:36]([CH3:42])([CH3:41])[CH2:37][C:38](Cl)=[O:39].Cl>C1COCC1.C(OCC)(=O)C>[NH:21]([C:19]([C:6]1[N:7]([CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:8]2[C:4]([CH:5]=1)=[CH:3][C:2]([NH:1][C:38](=[O:39])[CH2:37][C:36]([CH3:42])([CH3:41])[CH3:35])=[CH:10][CH:9]=2)=[O:20])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 815143,3-Dimethylbutanoyl chlorideHCID 23573455HCID 23573455, compound

Product 1

HCID 23573454HCID 23573454, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Under argon, 50 mg (0.14 mmol) of tert-butyl [5-amino-2-(anilinecarbonyl)-1H-indol-1-yl]acetate from Example LII and 15.23 mg (0.02 ml, 0.15 mmol) of triethylamine are added to 2 ml of THF. The mixture is cooled to 0° C., and a solution of 20.26 mg (0.02 ml, 0.15 mmol) of 3,3-dimethylbutyryl chloride in 0.2 ml of THF is added. The mixture is stirred at RT for 2 hours and, for work-up, added to dilute hydrochloric acid and ethyl acetate and extracted. The organic phase is washed with sat. sodium bicarbonate solution, dried with sodium sulphate, filtered and dried under reduced pressure. The resulting crude product is purified by column chromatography (silica gel 60, mobile phase: cyclohexane/ethyl acetate 2:1).

Workup

  1. extractionextracted
  2. washThe organic phase is washed with sat. sodium bicarbonate solution
  3. dry with materialdried with sodium sulphate
  4. filtrationfiltered
  5. customdried under reduced pressure
  6. customThe resulting crude product is purified by column chromatography (silica gel 60, mobile phase: cyclohexane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-cb5531fdbd104907b8545b182ae0738b
Source dataset
uspto-grants-2006_05
Patent number
US07045544B2

Reaction notes

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