Hydrochloric Acid → 2-[2,2-difluoro-2-(3-butoxyphenyl)-ethylamino]-N,N-dimethylpropanamide

HRID 62594노트

반응식

HRID 62594 반응식
C(OC([N:8]([CH2:16][C:17]([F:30])([F:29])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:19]=1)[CH:9]([CH3:15])[C:10]([N:12]([CH3:14])[CH3:13])=[O:11])=O)(C)(C)C.Cl>C(Cl)Cl.O1CCOCC1>[F:29][C:17]([F:30])([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:19]=1)[CH2:16][NH:8][CH:9]([CH3:15])[C:10]([N:12]([CH3:14])[CH3:13])=[O:11]

참가 물질

5

반응물 2

HCID 313Hydrochloric Acid3회HCID 711521052-[N-tert-butoxycarbonyl-2,2-difluoro-2-(3-butoxyphenyl)-ethylamino]-N,N-dimethylpropanamide

생성물 1

HCID 711520482-[2,2-difluoro-2-(3-butoxyphenyl)-ethylamino]-N,N-dimethylpropanamide

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매2회

실험 절차

84 mg (0.196 mmol) of 2-[N-tert-butoxycarbonyl-2,2-difluoro-2-(3-butoxyphenyl)-ethylamino]-N,N-dimethylpropanamide are dissolved in 3 mL of DCM and 0.49 mL (1.96 mmmol; 10 eq) of a 4M HCl solution in dioxane are added. After 8 hours, further 10 eq (0.49 mL) of 4M HCl 1 dioxane are added and the mixture is stirred overnight. Further 5 eq (0.245 mL) of 4M HCl in dioxane are the added and the mixture stirred for further 24 hours. The solution is evaporated, the white residue suspended in diethyl ether and then evaporated twice. The residue is flash-chromatographed on silica gel (DCM/MeOH 1/1 as an eluant followed by MeOH/conc. NH3 95/5). and the free base 2-[2,2-difluoro-2-(3-butoxyphenyl)-ethylamino]-N,N-dimethylpropanamide is isolated as a pale yellow fluid. The compound is dissolved in DCM (3 mL) and 4M HCl in dioxane is added to bring the solution to pH 2. The mixture is stirred for 10 minutes and then evaporated. The white residue is taken up with ether and evaporated twice. 45 mg (49%) of 2-[2,2-difluoro-2-(3-butoxyphenyl)-ethylamino]-N,N-dimethylpropanamide, hydrochloride (Example 2-1) are obtained.

후처리

  1. additionadded
  2. stirringthe mixture stirred for further 24 hours
  3. customThe solution is evaporated
  4. customevaporated twice
  5. customThe residue is flash-chromatographed on silica gel (DCM/MeOH 1/1 as an eluant

출처 및 근거

ORD 기록
ord-5496ee86950444659b30daa10c447879
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447029B2

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