Hydrochloric Acid → 2-(4-{[(3,4-Dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-N-methoxy-6-(methylsulfinyl)isonicotinamide

HRID 2233978Notes

Reaction equation

HRID 2233978 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]([C:18]2[CH:19]=[C:20]([CH:25]=[C:26]([S:28]([CH3:30])=[O:29])[N:27]=2)[C:21](OC)=[O:22])[CH2:14][CH2:13]1)=[O:10].[OH-].[Li+].Cl.Cl.[CH3:35][O:36][NH2:37]>C1COCC1>[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[CH2:13][CH2:14][N:15]([C:18]2[CH:19]=[C:20]([CH:25]=[C:26]([S:28]([CH3:30])=[O:29])[N:27]=2)[C:21]([NH:37][O:36][CH3:35])=[O:22])[CH2:16][CH2:17]1)=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 521874O-Methylhydroxylamine hydrochlorideHCID 68582437HCID 68582437, compound

Product 1

HCID 866083232-(4-{[(3,4-Dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-N-methoxy-6-(methylsulfinyl)isonicotinamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-6-(methylsulfinyl)isonicotinate (Example 334; 200 mg, 0.422 mmol) was dissolved in anhydrous THF (5 ml) and treated with 2 N lithium hydroxide (10 ml) with stirring for 45 minutes. The mixture was cooled in an ice bath and acidified with 1 N HCl. The aqueous solution was extracted with EtOAc. The organic phase was washed with water, dried over sodium sulfate and concentrated in vacuo to give the acid derivative as a brown solid (LCMS showed a peak of 459). This acid (95 mg, 0.207 mmol) was treated with methoxyamine hydrochloride (17.3 mg, 0.207 mmol) in a manner analogous to Example 8 to afford the title compound. (30 mg).

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. extractionThe aqueous solution was extracted with EtOAc
  3. washThe organic phase was washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give the acid derivative as a brown solid (LCMS

Sources & evidence

ORD record
ord-46483e9552ab4b32a0895a3c55acaa42
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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