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

HRID 1877944Notes

Reaction equation

HRID 1877944 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, 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).

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-b181c05c832043a1802a9df4bc6d376a
Source dataset
uspto-grants-2012_11
Patent number
US08314097B2

Reaction notes

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