Tryptamine → HCID 86589512, compound

HRID 1835112Notes

Reaction equation

HRID 1835112 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.C(=O)(OC(C)(C)C)OC(C)(C)C.C([O-])([O-])=O.[K+].[K+].ClC1N=C2N(C=1[S:40](Cl)(=[O:42])=[O:41])C=CS2.CC(C)([O-])C.[K+].C([O-])(O)=O.[Na+]>C1COCC1.O.CC(C)=O>[S:40](=[C:10]1[CH:11]=[C:12]2[C:7](=[N:6][CH:5]=[C:4]2[CH2:3][CH2:2][NH2:1])[CH:8]=[CH:9]1)(=[O:42])=[O:41]

Participants

10

Reactant 6

HCID 1150TryptamineHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 27997176-Chloroimidazo(2,1-b)(1,3)thiazole-5-sulfonyl chlorideHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 23665647Potassium tert-butoxide

Product 1

HCID 86589512HCID 86589512, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of tryptamine (4.2 g, 26.2 mmol) in a 1:1 mixture of acetone; water is treated with di-t-butyl carbonate (6.5 g, 27.8 mmol) and K2CO3 (7.5 g, 54.4 mmol), stirred at room temperature for 16 h, concentrated in vacuo to an aqueous mixture and extracted with EtOAc. The extracts are combined, dried over MgSO4 and concentrated in vacuo. A mixture of the resultant residue (5.6 g, 21 mmol) and 6-chloroimidazo[2,1-b]thiazole-5-sulfonyl chloride (5.01 g, 19.5 mmol) in THF is treated portion-wise with potassium t-butoxide (4.3 g, 39 mmol (2 eq.) at room temperature, stirred for 16 h, poured into a saturated NaHCO3 solution and extracted with EtOAc. The extracts are combined, dried over MgSO4 and concentrated in vacuo. This resultant residue is chromatographed (silica gel, 10%-60% EtOAc in hexanes as gradient eluent) to give the protected 5-sulfonyl-tryptamine intermediate as a tan solid, 5.6 g (60% yield). A solution of said intermediate (6.8 g 14.2 mmol) in isopropanol is treated with 4N HCl in dioxane (40 mL, 11 equiv.), stirred for 4 h and filtered. The filtercake is washed with ether and air-dried to give the title product as an off-white solid 3.2 g (55% yield) mp 239-241° C., identified by NMR and mass spectral analyses.

Workup

  1. concentrationconcentrated in vacuo to an aqueous mixture
  2. extractionextracted with EtOAc
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. stirringstirred for 16 h
  6. extractionextracted with EtOAc
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThis resultant residue is chromatographed (silica gel, 10%-60% EtOAc in hexanes as gradient eluent)

Sources & evidence

ORD record
ord-66991c9ced0a43f385589a1432a8efe7
Source dataset
uspto-grants-2004_08
Patent number
US06770642B2

Reaction notes

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