Trifluoroacetic acid → Baricitinib trifluoroacetate

HRID 1692898노트

반응식

HRID 1692898 반응식
[CH2:1]([S:3]([N:6]1[CH2:9][C:8]([CH2:32][C:33]#[N:34])([N:10]2[CH:14]=[C:13]([C:15]3[C:16]4[CH:23]=[CH:22][N:21](COCC[Si](C)(C)C)[C:17]=4[N:18]=[CH:19][N:20]=3)[CH:12]=[N:11]2)[CH2:7]1)(=[O:5])=[O:4])[CH3:2].[F:35][C:36]([F:41])([F:40])[C:37]([OH:39])=[O:38]>C(Cl)Cl>[F:35][C:36]([F:41])([F:40])[C:37]([OH:39])=[O:38].[CH2:1]([S:3]([N:6]1[CH2:9][C:8]([CH2:32][C:33]#[N:34])([N:10]2[CH:14]=[C:13]([C:15]3[C:16]4[CH:23]=[CH:22][NH:21][C:17]=4[N:18]=[CH:19][N:20]=3)[CH:12]=[N:11]2)[CH2:7]1)(=[O:4])=[O:5])[CH3:2]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 578688652-(1-(Ethylsulfonyl)-3-(4-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile

생성물 1

HCID 66824323Baricitinib trifluoroacetate수율 47%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 1-(ethylsulfonyl)-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-ylacetonitrile (0.111 g, 0.22 mmol) in methylene chloride (3 mL) was added trifluoroacetic acid (2 mL) and the solution was stirred for 1.5 hours. The solvents were removed in vacuo and the residue was dissolved in methanol (3 mL) and ethylenediamine (0.1 mL) was added. After stirring for 3 hours, the volume was reduced in vacuo and the product was purified by preparative-HPLC/MS, (SunFire C18 column, eluting with a gradient of MeCN/H2O containing 0.1% TFA) to afford the product as the trifluoroacetic acid salt (50 mg, 47%).

후처리

  1. customThe solvents were removed in vacuo
  2. dissolutionthe residue was dissolved in methanol (3 mL)
  3. additionethylenediamine (0.1 mL) was added
  4. stirringAfter stirring for 3 hours
  5. customthe product was purified by preparative-HPLC/MS, (SunFire C18 column
  6. washeluting with a gradient of MeCN/H2O containing 0.1% TFA)

출처 및 근거

ORD 기록
ord-6b6bd22a1c0145d79b83d2467c806b31
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158616B2

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