Water → 2-(4-{[(3,4-Dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3-thiazole-5-sulfonic acid

HRID 2234017Notes

Reaction equation

HRID 2234017 reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:19][CH:20]=[CH:21][N:22]=2)[CH2:14][CH2:13]1)=[O:10].Cl[S:24]([OH:27])(=[O:26])=[O:25].O>C(Cl)Cl>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][CH:12]1[CH2:13][CH2:14][N:15]([C:18]2[S:19][C:20]([S:24]([OH:27])(=[O:26])=[O:25])=[CH:21][N:22]=2)[CH2:16][CH2:17]1)=[O:10]

Participants

5

Reactant 3

HCID 962WaterHCID 24638Chlorosulfonic acidHCID 68579940HCID 68579940, compound

Product 1

HCID 866083382-(4-{[(3,4-Dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3-thiazole-5-sulfonic acidYield 46.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

3,4-Dichloro-5-methyl-N-[1-(1,3-thiazol-2-yl)piperidin-4-yl]-1H-pyrrole-2-carboxamide (Example 329; 692 mg, 1.93 mmol) was dissolved in anhydrous DCM. Chlorosulfonic acid (513 μl, 7.7 mmol) was added slowly and the mixture was heated at 60° C. for 2 h. The mixture was cooled to 0° C. and water was added, whereupon a brown solid separated. This was filtered and washed well with water, dried in vacuo to give the title compound (393 mg).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. customseparated
  3. filtrationThis was filtered
  4. washwashed well with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-f198197799c14b4d819b994c3314e51c
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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