Benzenesulfonyl chloride → HCID 59023876, compound

HRID 1678244Notes

Reaction equation

HRID 1678244 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][N:10]([CH3:22])[CH:11]=[N:12][C:13]1[CH:14]=[C:15]2[CH:21]=[CH:20][NH:19][C:16]2=[CH:17][N:18]=1.[C:23]1([S:29](Cl)(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[C:23]1([S:29]([N:19]2[C:16]3=[CH:17][N:18]=[C:13]([N:12]=[CH:11][N:10]([CH3:22])[CH3:9])[CH:14]=[C:15]3[C:21]([Br:1])=[CH:20]2)(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 10340Sodium CarbonateHCID 67184N-bromobutanimideHCID 10899400HCID 10899400, compound

Product 1

HCID 59023876HCID 59023876, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Bromo-pyrrolidine-2,5-dione (5.34 g, 30 mmol) was added to a stirred solution of N,N-dimethyl-N′-(1H-pyrrolo[2,3-c]pyridin-5-yl)-formamidine (Preparation #10b, 6.00 g, 31.9 mmol) in DMF (200 mL) at about 0° C. The reaction was allowed to warm to ambient temperature then stirred for about 1 hour. Benzenesulfonyl chloride (3.83 mL, 30.0 mmol) and Na2CO3 (6.36 g, 60.0 mmol) were added and the mixture was warmed at about 60° C. for about 1 hour. The reaction mixture was concentrated under reduced pressure and the dark solids were triturated with EtOAc (2×100 mL) and filtered. The combined EtOAc layers were passed through a 6 inch silica gel column, eluting with EtOAc. The product fractions were combined and concentrated to yield N′-(1-benzenesulfonyl-3-bromo-1H-pyrrolo[2,3-c]pyridin-5-yl)-N,N-dimethylformamidine (4.29 g, 35%) as a tan solid. RP HPLC (Table 1, Method e) Rt=2.18, m/z: (MH)+ 407/409.

Workup

  1. temperaturethe mixture was warmed at about 60° C. for about 1 hour
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe dark solids were triturated with EtOAc (2×100 mL)
  4. filtrationfiltered
  5. washeluting with EtOAc
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3cc5efc0d4c3467a89d443d2b194fd57
Source dataset
uspto-grants-2011_08
Patent number
US08008481B2

Reaction notes

Loading…