Sodium Carbonate → N-(1-aminopiperidin-4-yl)-3,4-dichloro-5-methyl-1H-pyrrole-2-carboxamide

HRID 2233876Notes

Reaction equation

HRID 2233876 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]([N:18]=O)[CH2:14][CH2:13]1)=[O:10].C([O-])([O-])=O.[Na+].[Na+]>O.CO>[NH2:18][N:15]1[CH2:16][CH2:17][CH:12]([NH:11][C:9]([C:3]2[NH:4][C:5]([CH3:8])=[C:6]([Cl:7])[C:2]=2[Cl:1])=[O:10])[CH2:13][CH2:14]1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 866082583,4-Dichloro-5-methyl-N-(1-nitrosopiperidin-4-yl)-1H-pyrrole-2-carboxamide2×

Product 1

HCID 68580041N-(1-aminopiperidin-4-yl)-3,4-dichloro-5-methyl-1H-pyrrole-2-carboxamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A 20% solution of TiCl3 (36 ml, 27 mmol) in water was added to a solution of 3,4-dichloro-5-methyl-N-(1-nitrosopiperidin-4-yl)-1H-pyrrole-2-carboxamide (Intermediate 87, 2.8 g, 9.2 mmol) in 60 ml of MeOH. The mixture was heated to 70° C. for 1 hour. Aqueous Na2CO3 was added to basify the mixture, which was filtered through Celite rinsing through with MeOH until no more material eluted. The filtrate was concentrated and the residual aqueous solution was saturated with NaCl before being extracted 6 times with DCM. The combined organic layers were dried (MgSO4) and solvent was removed to give product as a beige solid.

Workup

  1. filtrationwas filtered through Celite
  2. washrinsing through with MeOH until no more material
  3. washeluted
  4. concentrationThe filtrate was concentrated
  5. extractionbefore being extracted 6 times with DCM
  6. dry with materialThe combined organic layers were dried (MgSO4) and solvent
  7. customwas removed
  8. customto give product as a beige solid

Sources & evidence

ORD record
ord-6e971241c8ee4b128d34cd9039b5d86e
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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