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

HRID 62594ノート

反応式

HRID 62594 の反応式
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]

参加物

5

反応物 2

HCID 313Hydrochloric Acid3 回HCID 711521052-[N-tert-butoxycarbonyl-2,2-difluoro-2-(3-butoxyphenyl)-ethylamino]-N,N-dimethylpropanamide

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5496ee86950444659b30daa10c447879
出典データセット
uspto-grants-2016_09
特許番号
US09447029B2

反応ノート

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