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

HRID 2233978노트

반응식

HRID 2233978 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-46483e9552ab4b32a0895a3c55acaa42
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07709503B2

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