Hydrochloric Acid → HCID 22144651, compound

HRID 1824998Notes

Reaction equation

HRID 1824998 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:5]2.C(N(CC)CC)C.[CH3:29][C:30]([CH3:36])([CH3:35])[CH2:31][C:32](Cl)=[O:33].Cl>C1COCC1.C(OCC)(=O)C>[CH3:29][C:30]([CH3:36])([CH3:35])[CH2:31][C:32]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:5]2)=[O:33]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471Triethylamine2×HCID 815143,3-Dimethylbutanoyl chlorideHCID 22144642HCID 22144642, compound

Product 1

HCID 22144651HCID 22144651, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Under argon, 355 mg (1.27 mmol) of ethyl 5-amino-1-phenyl-1H-indole-2-carboxylate from Example LVII and 141 mg (0.19 ml, 1.39 mmol) of triethylamine are added to 4 ml of THF. The mixture is cooled to 0° C., and a solution of 170 mg (0.18 ml, 1.27 mmol) of 3,3-dimethylbutyryl chloride in 2 ml of THF is added. The mixture is stirred at RT for 2 hours. To bring the reaction to completion, a further 1 eq. of triethylamine and 1 eq. of acid chloride are added and the mixture is stirred at RT for 2 hours. For work-up, the mixture is 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 3:1-1:1).

Workup

  1. customthe reaction to completion
  2. stirringthe mixture is stirred at RT for 2 hours
  3. extractionextracted
  4. washThe organic phase is washed with sat. sodium bicarbonate solution
  5. dry with materialdried with sodium sulphate
  6. filtrationfiltered
  7. customdried under reduced pressure
  8. customThe resulting crude product is purified by column chromatography (silica gel 60, mobile phase: cyclohexane/ethyl acetate 3:1-1:1)

Sources & evidence

ORD record
ord-166bcbfcf3074a1e800f1e51b6df1848
Source dataset
uspto-grants-2006_05
Patent number
US07045544B2

Reaction notes

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