2-Methylpyrrolidine → HCID 24752212, compound

HRID 252249Notes

Reaction equation

HRID 252249 reaction equation
[Br:1][C:2]1[S:6][C:5]([NH:7][C:8]([NH:10][S:11]([C:14]2[CH:15]=[N:16][C:17](Cl)=[C:18]([Cl:20])[CH:19]=2)(=[O:13])=[O:12])=[O:9])=[N:4][CH:3]=1.[CH3:22][CH:23]1[CH2:27][CH2:26][CH2:25][NH:24]1>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[S:6][C:5]([NH:7][C:8]([NH:10][S:11]([C:14]2[CH:15]=[N:16][C:17]([N:24]3[CH2:25][CH2:26][CH2:27][CH:23]3[CH3:22])=[C:18]([Cl:20])[CH:19]=2)(=[O:13])=[O:12])=[O:9])=[N:4][CH:3]=1

Participants

5

Reactant 2

HCID 130032-MethylpyrrolidineHCID 86616718HCID 86616718, compound

Product 1

HCID 24752212HCID 24752212, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-[(5-Bromo-1,3-thiazol-2-yl)carbamoyl]-5,6-dichloropyridine-3-sulfonamide (20 mg, 0.05 mmol) was dissolved in DMF (1 ml) and reacted with 2-methylpyrrolidine (0.10 ml, 1 mmol) at 50° C. for 2.5 hours. The reaction mixture was diluted with ethyl acetate (30 ml) and washed with water, NaHCO3 (half sat. 3×), 5% KHSO4/10% K2SO4, NaCl sat., dried (MgSO4.2H2O), filtered and concentrated under reduced pressure. The crude was purified by preparative RP-HPLC: 6 mg, MS: m/e 477.9 (MH−).

Workup

  1. washwashed with water, NaHCO3 (half sat. 3×), 5% KHSO4/10% K2SO4, NaCl sat.
  2. dry with materialdried (MgSO4.2H2O)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude was purified by preparative RP-HPLC

Sources & evidence

ORD record
ord-6acb65e214e64c618b25e44eb3753406
Source dataset
uspto-grants-2011_01
Patent number
US07868030B2

Reaction notes

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