2-Methyl-1H-indole-3-ethylamine → HCID 69549439, compound

HRID 1793862Notes

Reaction equation

HRID 1793862 reaction equation
C[C:2]1[NH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:3]=1[CH2:4][CH2:5][NH2:6].[Cl:14][C:15]1[N:16]=[C:17]2[N:21]([C:22]=1[S:23](Cl)(=[O:25])=[O:24])[CH:20]=[CH:19][S:18]2.[CH3:27]C(C)([O-])C.[K+].C([O-])(O)=O.[Na+]>C1COCC1>[ClH:14].[Cl:14][C:15]1[N:16]=[C:17]2[N:21]([C:22]=1[S:23]([N:13]1[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:3]([CH2:4][C@@H:5]([NH2:6])[CH3:27])=[CH:2]1)(=[O:25])=[O:24])[CH:20]=[CH:19][S:18]2

Participants

6

Reactant 4

HCID 759492-Methyl-1H-indole-3-ethylamineHCID 516892Sodium BicarbonateHCID 27997176-Chloroimidazo(2,1-b)(1,3)thiazole-5-sulfonyl chlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 69549439HCID 69549439, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (S)-2-(1H-Indol-3-yl)-1-methylethylamine (0.43 g, 2.5 mmol) and di-t-butyl dicarbonate (0.60 g, 2.75 mmol) in acetone is treated dropwise with aqueous K2CO3 (3.5 g, 25 mmol) at OC, allowed to warm to room temperature for 16 h, concentrated to an aqueous residue and extracted with EtOAc. The extracts are combined, dried over MgSO4 and concentrated in vacuo to dryness. This residue is chromatographed (silica gel, 10%–50% EtOAc in hexanes as gradient eluent) to give the protected ®-2-methyl tryptamine. A mixture of the protected tryptamine (0.17 g, 0.62 mmol) and 6-chloroimidazo[2,1-b]thiazole-5-sulfonyl chloride (0.16 g, 0.62 mmol) in THF is treated with potassium t-butoxide (77 mg, 0.68 mmol) at room temperature, stirred for 1H, poured into saturated NaHCO3 and extracted with EtOAc. The extracts are combined, dried over Na2SO4 and concentrated in vacuo. The resultant residue is dispersed in THF and 4N HCl in dioxane, stirred for 16 h, concentrated in vacuo and purified by HPLC1 to afford the title product as a beige solid, 0.62 mg (35% yield), identified by NMR and mass spectral analyses. 1HPLC conditions: Hewlett Packard 1100 HPLC system; Waters Xterra C18, 2 mm×30 mm ID, 3 uM column; 5 uL injection; Solvent A: 0.02% TFA/water; Solvent B: 0.02% TFA/acetonitrile; Gradient: Time 0: 95% A; 0.2 min: 95% A; 3 min: 5% A; Flow rate 1.2 mL/min; Detection: 254 nm DAD.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. additionThe resultant residue is dispersed in THF
  5. stirring4N HCl in dioxane, stirred for 16 h
  6. concentrationconcentrated in vacuo
  7. custompurified by HPLC1

Sources & evidence

ORD record
ord-78f647a6ce0d46c1b64cf19a067420c6
Source dataset
uspto-grants-2006_04
Patent number
US07022701B2

Reaction notes

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