Hydrochloric Acid → HCID 58557085, compound

HRID 1969536Notes

Reaction equation

HRID 1969536 reaction equation
[H-].[Na+].[Br:3][C:4]1[N:5]=[C:6]([C:11]#[C:12][CH3:13])[C:7]([NH2:10])=[N:8][CH:9]=1.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.Cl>CN1C(=O)CCC1>[Br:3][C:4]1[N:5]=[C:6]2[CH:11]=[C:12]([CH3:13])[N:10]([S:20]([C:17]3[CH:18]=[CH:19][C:14]([CH3:24])=[CH:15][CH:16]=3)(=[O:22])=[O:21])[C:7]2=[N:8][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 58557512HCID 58557512, compound

Product 1

HCID 58557085HCID 58557085, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent3×

Procedure

To a slurry of NaH (60% dispersion in mineral oil, 2.00 g, 49.9 mmol) in NMP (100 mL) was slowly added a solution of 5-bromo-3-(prop-1-ynyl)pyrazin-2-amine (7.05 g, 33.2 mmol) in NMP (20 mL). The reaction mixture was stirred at ambient temperature for about 20 min and then a solution of p-toluenesulfonyl chloride (6.97 g, 36.6 mmol) in NMP (20 mL) was added. The reaction mixture was stirred at ambient temperature for about 20 h and then aqueous HCl (1 N, 100 mL) was added to the reaction mixture. The resulting solids were collected by filtration. The brown solid was triturated with DCM/EtOAc (1:1, 30 mL) and collected by filtration to provide 2-bromo-6-methyl-5-tosyl-5H-pyrrolo[2,3-b]pyrazine (9.0 g, 74%) as a brown solid: LC/MS (Table 1, Method a) Rt=2.68 min; MS m/z: 366, 368 (1:1) (M+H)+.

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for about 20 h
  2. filtrationThe resulting solids were collected by filtration
  3. customThe brown solid was triturated with DCM/EtOAc (1:1, 30 mL)
  4. filtrationcollected by filtration

Sources & evidence

ORD record
ord-3fbcf2bad75649dfa6607d9ee2b6c066
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

Loading…