Ammonia dioxane → N-{1-[5-(Aminosulfonyl)-1,3-thiazol-2-yl]piperidin-4-yl}-3,4-dichloro-5-methyl-1H-pyrrole-2-carboxamide

HRID 2234018Notes

Reaction equation

HRID 2234018 reaction equation
[NH3:1].O1CCOCC1.[Cl:8][C:9]1[C:13]([Cl:14])=[C:12]([CH3:15])[NH:11][C:10]=1[C:16]([NH:18][CH:19]1[CH2:24][CH2:23][N:22]([C:25]2[S:26][C:27]([S:30]([OH:33])(=O)=[O:31])=[CH:28][N:29]=2)[CH2:21][CH2:20]1)=[O:17]>>[NH2:1][S:30]([C:27]1[S:26][C:25]([N:22]2[CH2:23][CH2:24][CH:19]([NH:18][C:16]([C:10]3[NH:11][C:12]([CH3:15])=[C:13]([Cl:14])[C:9]=3[Cl:8])=[O:17])[CH2:20][CH2:21]2)=[N:29][CH:28]=1)(=[O:33])=[O:31]

Participants

3

Reactant 2

HCID 66648793Ammonia dioxaneHCID 866083382-(4-{[(3,4-Dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3-thiazole-5-sulfonic acid

Product 1

HCID 68580500N-{1-[5-(Aminosulfonyl)-1,3-thiazol-2-yl]piperidin-4-yl}-3,4-dichloro-5-methyl-1H-pyrrole-2-carboxamideYield 56.5%

Procedure

0.5 M ammonia/dioxane (10 ml, 5 mmol) was added to 2-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3-thiazole-5-sulfonic acid (Example 254; 100 mg, 0.226 mmol) in a pressure bottle. The mixture was stirred at room temperature for 4 h. Excess solvent was removed in vacuo and the brown solid was dried in vacuo to give the title compound (56 mg).

Workup

  1. customExcess solvent was removed in vacuo
  2. customthe brown solid was dried in vacuo

Sources & evidence

ORD record
ord-23a33f93735e4a5aa0b7835d5f45fe8b
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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