Trifluoroacetic acid → Baricitinib trifluoroacetate

HRID 1692898ノート

反応式

HRID 1692898 の反応式
[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]

参加物

4

反応物 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

生成物 1

HCID 66824323Baricitinib trifluoroacetate収率 47%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-6b6bd22a1c0145d79b83d2467c806b31
出典データセット
uspto-grants-2012_04
特許番号
US08158616B2

反応ノート

読み込み中…