1,2-Dichloroethane → 2-(4-{[(4-Bromo-5-ethyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-6-chloroisonicotinamide

HRID 2233916Notes

Reaction equation

HRID 2233916 reaction equation
C(N(C(C)C)CC)(C)C.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.[Br:24][C:25]1[CH:26]=[C:27]([C:32]([OH:34])=O)[NH:28][C:29]=1[CH2:30][CH3:31].Cl.[NH2:36][CH:37]1[CH2:42][CH2:41][N:40]([C:43]2[CH:44]=[C:45]([CH:49]=[C:50]([Cl:52])[N:51]=2)[C:46]([NH2:48])=[O:47])[CH2:39][CH2:38]1>CN(C=O)C>[Br:24][C:25]1[CH:26]=[C:27]([C:32]([NH:36][CH:37]2[CH2:38][CH2:39][N:40]([C:43]3[CH:44]=[C:45]([CH:49]=[C:50]([Cl:52])[N:51]=3)[C:46]([NH2:48])=[O:47])[CH2:41][CH2:42]2)=[O:34])[NH:28][C:29]=1[CH2:30][CH3:31]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 685798234-Bromo-5-ethyl-1H-pyrrole-2-carboxylic acid2×HCID 86608255HCID 86608255, compound2×

Product 1

HCID 866082712-(4-{[(4-Bromo-5-ethyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-6-chloroisonicotinamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Diisopropylethylamine (0.28 ml, 1.64 mmol), EDC (0.088 g, 0.46 mmol) and HOAT (0.063 g, 0.46 mmol) were added to a stirred solution of 4-bromo-5-ethyl-1H-pyrrole-2-carboxylic acid (Intermediate 10, 0.1 g, 0.46 mmol) in DMF (1.5 ml) at room temperature. The resultant solution was stirred for 30 mins and a solution of 2-(4-aminopiperidin-1-yl)-6-chloroisonicotinamide hydrochloride (Intermediate 70, 0.14 g, 0.55 mmol) in 3 ml of DMF was added. The reaction was stirred overnight, then concentrated under vacuum and the residue was partitioned between water and EtOAc. The aqueous layer was extracted with EtOAc (×2) and the combined organic extracts were washed with 1 N HCl, water and brine, dried over MgSO4 and concentrated under vacuum. The residue was purified by reverse phase chromatography to give the desired product as a white solid.

Workup

  1. concentrationconcentrated under vacuum
  2. customthe residue was partitioned between water and EtOAc
  3. extractionThe aqueous layer was extracted with EtOAc (×2)
  4. washthe combined organic extracts were washed with 1 N HCl, water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-31287a23d0ee41f99b3c29558c475577
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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