Pyrrolidine → (2-Chloro-5-phenyl-thiophen-3-yl)-(pyrrolidin-1-yl)-methanone

HRID 2068600ノート

反応式

HRID 2068600 の反応式
[Cl:1][C:2]1[S:3][C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][C:6]=1[C:7]([OH:9])=O.CC[N:18]([CH:22]([CH3:24])C)[CH:19]([CH3:21])C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N1CCCC1>CN(C=O)C>[Cl:1][C:2]1[S:3][C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][C:6]=1[C:7]([N:18]1[CH2:19][CH2:21][CH2:24][CH2:22]1)=[O:9]

参加物

6

反応物 4

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 581102042-Chloro-5-phenylthiophene-3-carboxylic acid

生成物 1

HCID 44226477(2-Chloro-5-phenyl-thiophen-3-yl)-(pyrrolidin-1-yl)-methanone収率 252.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

2-Chloro-5-phenyl-thiophene-3-carboxylic acid (28 mg, 0.11 mmol) was dissolved in DMF (1 mL). DIPEA (0.22 mmol), HATU (0.11 mmol) and pyrrolidine (0.11 mmol) were added and the reaction mixture stirred at room temperature. The reaction mixture was partitioned between ethyl acetate and 1 N hydrochloric acid. The organic solution was separated and dried over magnesium sulfate, filtered and the solvent evaporated. The residue was purified by preparative HPLC, eluting with 50%-90% acetonitrile in water (0.1% formic acid) over 30 minutes. The fractions containing the desired product were concentrated under vacuum to give the title compound (81 mg). LCMS m/z 292.10 [M+H]+R.T.=11.27 mins (Analytical Method 1)

後処理

  1. customThe reaction mixture was partitioned between ethyl acetate and 1 N hydrochloric acid
  2. customThe organic solution was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent evaporated
  6. customThe residue was purified by preparative HPLC
  7. washeluting with 50%-90% acetonitrile in water (0.1% formic acid) over 30 minutes
  8. additionThe fractions containing the desired product
  9. concentrationwere concentrated under vacuum

出典と根拠

ORDレコード
ord-bc604fa0b13b48d6ae4ce6036fb7901b
出典データセット
uspto-grants-2012_10
特許番号
US08299063B2

反応ノート

読み込み中…