Pyridine → N-((6-bromothiazolo[5,4-b]pyridin-2-yl)methyl)methanesulfonamide

HRID 525601Notes

Reaction equation

HRID 525601 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([CH2:11][NH2:12])[S:8][C:5]2=[N:6][CH:7]=1.N1C=CC=CC=1.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([CH2:11][NH:12][S:20]([CH3:19])(=[O:22])=[O:21])[S:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 86695491(6-Bromothiazolo[5,4-b]pyridin-2-yl)methanamine

Product 1

HCID 86695490N-((6-bromothiazolo[5,4-b]pyridin-2-yl)methyl)methanesulfonamideYield 75.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (ice-water) solution of (6-bromothiazolo[5,4-b]pyridin-2-yl)methanamine (800 mg, 3.28 mmol) and pyridine (800 mg, 9.85 mmol) in CH2Cl2 (10 mL) is slowly added methanesulfonyl chloride (380 mg, 3.28) and stirred at room temperature for 3 hours. Reaction mixture is washed with water (2×10 mL) dried over Na2SO4 and concentrated. Obtained crude product purified on silica gel column using 0 to 5% methanol/CH2Cl2 to give the title compound (800 mg): m/z (Cl) M+2 324.

Workup

  1. customReaction mixture
  2. washis washed with water (2×10 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customObtained crude product
  6. custompurified on silica gel column

Sources & evidence

ORD record
ord-4a75f0c70b86494f9741152c3b33726d
Source dataset
uspto-grants-2016_05
Patent number
US09340564B2

Reaction notes

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