3,4-dichloro-N-[1-(5-cyano-4-hydroxy-1,3-thiazol-2-yl)piperidin-4-yl]-5-methyl-1H-pyrrole-2-carboxamide → 2-(4-{[(3,4-Dichloro-5-cyano-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3-thiazole-5-carboxylic acid

HRID 2234030Notes

Reaction equation

HRID 2234030 reaction equation
ClC1C(Cl)=C(C)NC=1C(NC1CCN(C2SC(C#N)=C(O)N=2)CC1)=O.[Cl:26][C:27]1[C:31]([Cl:32])=[C:30]([C:33]#[N:34])[NH:29][C:28]=1[C:35]([NH:37][CH:38]1[CH2:43][CH2:42][N:41]([C:44]2[S:45][C:46]([C:49]([O:51]C)=[O:50])=[CH:47][N:48]=2)[CH2:40][CH2:39]1)=[O:36]>>[Cl:26][C:27]1[C:31]([Cl:32])=[C:30]([C:33]#[N:34])[NH:29][C:28]=1[C:35]([NH:37][CH:38]1[CH2:43][CH2:42][N:41]([C:44]2[S:45][C:46]([C:49]([OH:51])=[O:50])=[CH:47][N:48]=2)[CH2:40][CH2:39]1)=[O:36]

Participants

3

Reactant 2

HCID 685798543,4-dichloro-N-[1-(5-cyano-4-hydroxy-1,3-thiazol-2-yl)piperidin-4-yl]-5-methyl-1H-pyrrole-2-carboxamideHCID 68580069Methyl 2-(4-{[(3,4-dichloro-5-cyano-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3-thiazole-5-carboxylate

Product 1

HCID 685799672-(4-{[(3,4-Dichloro-5-cyano-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3-thiazole-5-carboxylic acid

Procedure

The title compound was prepared by a procedure analogous to Intermediate 3 starting from methyl 2-(4-{[(3,4-dichloro-5-cyano-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3-thiazole-5-carboxylate (Example 271). The reaction mixture was concentrated to remove MeOH. Water was added and the pH was adjusted to pH 4 with NaHCO3. The product was extracted with CHCl3:isopropanol (3:1). Drying (MgSO4) and removal of solvent yielded a white solid. The was dried in drying pistol at 75° C. under vacuum.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto remove MeOH
  3. additionWater was added
  4. extractionThe product was extracted with CHCl3:isopropanol (3:1)
  5. customDrying
  6. custom(MgSO4) and removal of solvent
  7. customyielded a white solid
  8. customThe was dried
  9. customin drying pistol at 75° C. under vacuum

Sources & evidence

ORD record
ord-c44de14da1bf44e58e92b2b3a1d3f377
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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