Cyclopropylamine → HCID 10262802, compound

HRID 1642735Notes

Reaction equation

HRID 1642735 reaction equation
Cl[CH2:2][C:3]([N:5]1[C@@H:9]([C:10]#[CH:11])[CH2:8][CH2:7][C@H:6]1[C:12]#[N:13])=[O:4].[CH:14]1([NH2:17])[CH2:16][CH2:15]1>C(#N)C>[CH:14]1([NH:17][CH2:2][C:3]([N:5]2[C@@H:9]([C:10]#[CH:11])[CH2:8][CH2:7][C@H:6]2[C:12]#[N:13])=[O:4])[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 16090854(2S,5R)-1-(2-chloroacetyl)-5-ethynylpyrrolidine-2-carbonitrile

Product 1

HCID 10262802HCID 10262802, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of Example 8D (0.045 g, 0.228 mmol) in acetonitrile (2 mL) at room temperature under nitrogen was added cyclopropylamine (0.032 ml, 0.457 mmol). The reaction mixture was stirred overnight and then concentrated under reduced pressure. The residue was flash chromatographed with 3% MeOH/CH2Cl2 to provide the desired compound as a pale yellow oil. MS m/z 218 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 1.5-2 (4H, m), 2.11-2.21 (2H, m), 2.45-2.48 (2H, m), 3.78 (1H, d), 3.8-4.5 (2H, m), 4.53-4.55 (1H, t), 5.01 (1H, m), 5.05 (1H, m).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customchromatographed with 3% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-ab8232730c144864b310ab78920891a3
Source dataset
uspto-grants-2012_02
Patent number
US08119664B2

Reaction notes

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