Ethanol → 3-amino-4-(6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)benzonitrile

HRID 1877944ノート

反応式

HRID 1877944 の反応式
[CH:1]1[N:5]=[CH:4][N:3]2[CH:6]([C:9]3[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][C:10]=3[N+:17]([O-])=O)[CH2:7][CH2:8][C:2]=12.CCO>C1COCC1.[Pd]>[NH2:17][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:9]=1[CH:6]1[N:3]2[CH:4]=[N:5][CH:1]=[C:2]2[CH2:8][CH2:7]1)[C:13]#[N:14]

参加物

5

反応物 2

HCID 702EthanolHCID 588271134-(6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)-3-nitrobenzonitrile

生成物 1

HCID 588270433-amino-4-(6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)benzonitrile

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8028Tetrahydrofuran溶媒

実験手順

4-(6,7-Dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)-3-nitrobenzonitrile (0.054 g, 0.212 mmol) is dissolved in THF (2 mL) and EtOH (2 mL) and 5% palladium on carbon (wet) (15 mg) is then added. The mixture is placed under an atmosphere of hydrogen overnight. The mixture is then filtered and concentrated. The residue is purified via HPLC (reversed phase, CH3CN/H2O) to give 3-amino-4-(6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)benzonitrile as a solid. MS (ESI) m/z 225.0 (M+H); 1H NMR (400 MHz, CH3CN) (TFA salt) δ ppm 2.45-2.57 (m, 1 H), 2.99-3.16 (m, 3 H), 4.47 (br s, 2 H), 5.68-5.75 (m, 1 H), 6.69 (d, J=7.8 Hz, 1 H), 6.98 (d, J=1.5 Hz, 1 H), 7.09 (d, J=1.8 Hz, 1 H), 7.21 (s, 1 H), 8.32 (s, 1 H).

後処理

  1. filtrationThe mixture is then filtered
  2. concentrationconcentrated
  3. customThe residue is purified via HPLC (reversed phase, CH3CN/H2O)

出典と根拠

ORDレコード
ord-b181c05c832043a1802a9df4bc6d376a
出典データセット
uspto-grants-2012_11
特許番号
US08314097B2

反応ノート

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