Hydrochloric Acid → HCID 72480284, compound

HRID 1182066Notes

Reaction equation

HRID 1182066 reaction equation
[Br:1][C:2]1[C:3]([NH:9][C@H:10]([CH3:13])[CH2:11][OH:12])=[N:4][C:5](Cl)=[N:6][CH:7]=1.[NH2:14][C:15]1[CH:16]=[C:17]([S:20]([F:23])(=[O:22])=[O:21])[S:18][CH:19]=1.NC1SC(S(F)(=O)=O)=CC=1.Cl>C(#N)C.O.O1CCOCC1>[Br:1][C:2]1[C:3]([NH:9][CH:10]([CH3:13])[CH2:11][OH:12])=[N:4][C:5]([NH:14][C:15]2[CH:16]=[C:17]([S:20]([F:23])(=[O:22])=[O:21])[S:18][CH:19]=2)=[N:6][CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 58890883HCID 58890883, compoundHCID 58981886HCID 58981886, compoundHCID 58981929HCID 58981929, compound

Product 1

HCID 72480284HCID 72480284, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Procedure

324 mg (1.2 mmol) of (R)-2-(5-bromo-2-chloro-pyrimidin-4-ylamino)-propan-1-ol is added to a suspension of 330 mg of a mixture that consists of 4-amino-thiophene-2-sulfonyl fluoride and 5-amino-thiophene-2-sulfonyl fluoride (ratio: 3:1) in 5 ml of acetonitrile, 0.5 ml of water and 0.5 ml of a 4 molar solution of hydrochloric acid in 1,4-dioxane. The reaction mixture is stirred under reflux for 26 hours. After cooling, the batch is concentrated by evaporation, and the residue is stirred with ethanol. The precipitate that is formed is suctioned off and stirred with warm water. In turn, the solid is suctioned off and dried. 152 mg (0.37 mmol, 31% of theory) of the product 4-[5-bromo-4-(2-hydroxy-1-methyl-ethylamino)-pyrimidin-2-ylamino]-thiophene-2-sulfonyl fluoride is obtained.

Workup

  1. temperatureunder reflux for 26 hours
  2. temperatureAfter cooling
  3. concentrationthe batch is concentrated by evaporation
  4. stirringthe residue is stirred with ethanol
  5. customThe precipitate that is formed
  6. customdried

Sources & evidence

ORD record
ord-e383fbd1e50f4dbc91c639eedf3bebd6
Source dataset
uspto-grants-2007_10
Patent number
US07288547B2

Reaction notes

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