Sodium Hydroxide → 1-[4-Dimethylamino-2-(2-methylsulfanyl-pyrimidine-4-carbonyl) pyrazolidin-1-yl]-2-(4-fluorophenyl)-ethanone

HRID 22676

반응식

HRID 22676 반응식
[CH3:1][N:2]([CH3:18])[CH:3]1[CH2:7][N:6]([C:8](=[O:17])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[NH:5][CH2:4]1.[CH3:19][S:20]([C:23]1[N:28]=[C:27]([C:29](Cl)=[O:30])[CH:26]=[CH:25][N:24]=1)(=O)=O.[OH-].[Na+]>ClCCl>[CH3:18][N:2]([CH3:1])[CH:3]1[CH2:7][N:6]([C:8](=[O:17])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[N:5]([C:29]([C:27]2[CH:26]=[CH:25][N:24]=[C:23]([S:20][CH3:19])[N:28]=2)=[O:30])[CH2:4]1

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 219921942-Methylsulfonyl-pyrimidine-4-carbonyl chlorideHCID 219921971-(4-Dimethylamino-pyrazolidin-1-yl)-2-(4-fluorophenyl)-ethanone

생성물 1

HCID 219922051-[4-Dimethylamino-2-(2-methylsulfanyl-pyrimidine-4-carbonyl) pyrazolidin-1-yl]-2-(4-fluorophenyl)-ethanone

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 1-(4-dimethylamino-pyrazolidin-1-yl)-2-(4-fluorophenyl)-ethanone, 22, (2.5 g, 10 mmol) in dichloromethane (20 mL) is added 2-methylsulfonyl-pyrimidine-4-carbonyl chloride (3.7 g, 20 mmol) followed by dropwise addition of a 1.0 N aqueous solution of sodium hydroxide (35 mL). The mixture is vigorously stirred at room temperature for 12 hours. The reaction is diluted with dichloromethane (100 mL) and washed with water (100 mL). The aqueous layer is back-extracted with dichloromethane (100 mL). The combined organic layers are washed with a saturated aqueous solution of sodium bicarbonate (100 mL) and brine (100 mL), dried, filtered and concentrated in vacuo. The resulting crude material is purified over silica (1:1 hexane/ethyl acetate to 100% ethyl acetate) to afford the desired product.

후처리

  1. washwashed with water (100 mL)
  2. extractionThe aqueous layer is back-extracted with dichloromethane (100 mL)
  3. washThe combined organic layers are washed with a saturated aqueous solution of sodium bicarbonate (100 mL) and brine (100 mL)
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting crude material is purified over silica (1:1 hexane/ethyl acetate to 100% ethyl acetate)

출처 및 근거

ORD 기록
ord-1aac72309af94aed9087878baba4662c
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06849627B2

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