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Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → (4,4-Difluoro-azepan-1-yl)-(5-phenyl-thiophen-3-yl)-methanone

HRID 1914591
ノート
印刷プレビュー

反応式

HRID 1914591 の反応式
[C:1]1([C:7]2[S:11][CH:10]=[C:9]([C:12]([OH:14])=O)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[F:16][C:17]1([F:24])[CH2:23][CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(#N)C>[F:16][C:17]1([F:24])[CH2:23][CH2:22][CH2:21][N:20]([C:12]([C:9]2[CH:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[S:11][CH:10]=2)=[O:14])[CH2:19][CH2:18]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 162272215-Phenylthiophene-3-carboxylic acidHCID 569243114,4-Difluoroazepane hydrochloride

生成物 1

HCID 44226682(4,4-Difluoro-azepan-1-yl)-(5-phenyl-thiophen-3-yl)-methanone収率 42%

試薬・触媒・溶媒 1

HCID 6342
Acetonitrile
溶媒

実験手順

5-Phenyl-thiophene-3-carboxylic acid (0.20 g, 1.11 mmol) and 4,4-difluoro-azepane hydrochloride (0.19 g, 1.11 mmol) were stirred in acetonitrile (10 mL) with silica-supported diethylamine (1.32 mmol/g, 2.5 g) and HATU (0.40 g, 1.11 mmol) for 18 hours. The reaction mixture was filtered and the solvent was removed by evaporation then the crude material was purified by HPLC, eluting with 10%-98% acetonitrile in water (0.1% formic acid) over 20 minutes. The fractions containing the desired product were evaporated to give the title compound as a gum (0.15 g). LCMS m/z 322.19 [M+H]+ R.T.=11.14 min (Analytical Method 2).

後処理

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was removed by evaporation
  3. customthe crude material was purified by HPLC
  4. washeluting with 10%-98% acetonitrile in water (0.1% formic acid) over 20 minutes
  5. additionThe fractions containing the desired product
  6. customwere evaporated

出典と根拠

ORDレコード
ord-ae6a2e4df26445c8bcb3e58312c4873b
出典データセット
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08614209B2

反応ノート

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