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

HRID 923264Notes

Reaction equation

HRID 923264 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

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, 1H), 2.99-3.16 (m, 3H), 4.47 (br s, 2H), 5.68-5.75 (m, 1H), 6.69 (d, J=7.8 Hz, 1H), 6.98 (d, J=1.5 Hz, 1H), 7.09 (d, J=1.8 Hz, 1H), 7.21 (s, 1H), 8.32 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-e835f0ca087343c1a1321804e459f101
Source dataset
uspto-grants-2016_03
Patent number
US09278969B2

Reaction notes

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