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

HRID 2233978ノート

反応式

HRID 2233978 の反応式
[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]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 521874O-Methylhydroxylamine hydrochlorideHCID 68582437HCID 68582437、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-46483e9552ab4b32a0895a3c55acaa42
出典データセット
uspto-grants-2010_05
特許番号
US07709503B2

反応ノート

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