Cyclopropylamine → Methyl 3-chloro-5-[(cyclopropylamino)carbonyl]-1H-pyrrole-2-carboxylate

HRID 1874970ノート

反応式

HRID 1874970 の反応式
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[Cl:5][C:6]1[CH:10]=[C:9]([C:11](Cl)=[O:12])[NH:8][C:7]=1[C:14]([O:16][CH3:17])=[O:15]>C1COCC1>[Cl:5][C:6]1[CH:10]=[C:9]([C:11]([NH:4][CH:1]2[CH2:3][CH2:2]2)=[O:12])[NH:8][C:7]=1[C:14]([O:16][CH3:17])=[O:15]

参加物

4

反応物 2

HCID 69828CyclopropylamineHCID 86644903Methyl 3-chloro-5-(chlorocarbonyl)-1H-pyrrole-2-carboxylate

生成物 1

HCID 68484245Methyl 3-chloro-5-[(cyclopropylamino)carbonyl]-1H-pyrrole-2-carboxylate収率 70.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Cycloproplyamine (0.166 g, 2.90 mmol) was added to a solution of methyl 3-chloro-5-(chlorocarbonyl)-1H-pyrrole-2-carboxylate (0.150 g, 0.580 mmol) in THF and the resulting solution stirred until no starting material was evident by TLC. The solvent was evaporated and purification was accomplished by silica gel column chromatography (30-100% EtOAc/hexanes) to afford the title compound (0.099 g, 70%) as a white solid. 1H NMR (400 MHz, Acetone-d6) δ ppm 10.81 (br. s., 1H), 7.71 (br. s., 1H), 6.78 (s, 1H), 3.84 (s, 3H), 2.79-2.92 (m, 1H), 0.73 (d, 2H), 0.57 (d, 2 H) LCMS: m/z 243.1 (M+1).

後処理

  1. customThe solvent was evaporated
  2. custompurification

出典と根拠

ORDレコード
ord-ea2b2e9b11064fb083e91dc628a5f7d5
出典データセット
uspto-grants-2012_11
特許番号
US08304419B2

反応ノート

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