Hydrochloric Acid → HCID 67998792, compound

HRID 1969529Notes

Reaction equation

HRID 1969529 reaction equation
[N:1]([CH:4]([C:8]1[N:9]=[C:10]2[CH:16]=[CH:15][N:14]([S:17]([C:20]3[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[C:11]2=[N:12][CH:13]=1)[CH2:5][CH:6]=[CH2:7])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[ClH:46].CCOCC>C1COCC1.O.CCOC(C)=O>[ClH:46].[S:17]([N:14]1[C:11]2=[N:12][CH:13]=[C:8]([CH:4]([NH2:1])[CH2:5][CH:6]=[CH2:7])[N:9]=[C:10]2[CH:16]=[CH:15]1)([C:20]1[CH:21]=[CH:22][C:23]([CH3:24])=[CH:25][CH:26]=1)(=[O:18])=[O:19]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 11776TriphenylphosphineHCID 585572372-(1-azidobut-3-enyl)-5-tosyl-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 67998792HCID 67998792, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-(1-azidobut-3-enyl)-5-tosyl-5H-pyrrolo[2,3-b]pyrazine (3.90 g, 10.6 mmol) in THF (60 mL) and water (30 mL) was added triphenylphosphine (3.33 g, 12.7 mmol). The reaction mixture was heated to about 50° C. for about 15 h. The reaction mixture was cooled to ambient temperature and concd in vacuo. The residue was dissolved in EtOAc (30 mL) and HCl (gas) was added until a pH of about 1 was maintained followed by the addition of Et2O to induce precipitate formation. After stirring for about 15 h, the precipitate was collected by filtration to provide 1-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)but-3-en-1-amine hydrochloride (2.5 g, 62%) as a tan solid: LC/MS (Table 1, Method a) Rt=1.80 min; MS m/z: 343 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. temperaturewas maintained
  3. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-527670cf3c8d498eb6c6f9fd61171916
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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