Hydrochloric Acid → 2-(4-{[(3,4-Dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-6-[2-(dimethylamino)ethoxy]isonicotinic acid

HRID 2233975Notes

Reaction equation

HRID 2233975 reaction equation
[Na].[CH3:2][N:3]([CH3:7])[CH2:4][CH2:5][OH:6].Cl[C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([N:19]2[CH2:24][CH2:23][CH:22]([NH:25][C:26]([C:28]3[NH:29][C:30]([CH3:35])=[C:31]([Cl:34])[C:32]=3[Cl:33])=[O:27])[CH2:21][CH2:20]2)[N:18]=1)[C:12]([O:14]C)=[O:13].Cl>CN(C=O)C>[Cl:33][C:32]1[C:31]([Cl:34])=[C:30]([CH3:35])[NH:29][C:28]=1[C:26]([NH:25][CH:22]1[CH2:23][CH2:24][N:19]([C:17]2[CH:16]=[C:11]([CH:10]=[C:9]([O:6][CH2:5][CH2:4][N:3]([CH3:7])[CH3:2])[N:18]=2)[C:12]([OH:14])=[O:13])[CH2:20][CH2:21]1)=[O:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 79022-(Dimethylamino)ethanolHCID 5360545SodiumHCID 86608321Methyl 2-chloro-6-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)isonicotinate

Product 1

HCID 685799072-(4-{[(3,4-Dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-6-[2-(dimethylamino)ethoxy]isonicotinic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium (155 mg, 6.74 mmol) and 2-(dimethylamino)ethanol (0.677 ml, 6.74 mmol) were stirred together in DMF (1.5 ml). Methyl 2-chloro-6-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)isonicotinate (Example 333; 200 mg, 0.449 mmol) was added. The reaction mixture was refluxed overnight, then brought to room temperature and acidified with 10% HCl. The reaction mixture was partitioned between EtOAc and water. The organic layer was washed with water, then with brine, dried over sodium sulfate and concentrated to give the desired product. The crude product was purified by reversed phase HPLC eluting with water/acetonitrile/TFA mixtures to afford the desired product (60 mg).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. custombrought to room temperature
  3. customThe reaction mixture was partitioned between EtOAc and water
  4. washThe organic layer was washed with water
  5. dry with materialwith brine, dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4367a1e4a5ba49af88bea1fb698e7c9b
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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