Cyclopentylamine → HCID 10243173, compound

HRID 1293412Notes

Reaction equation

HRID 1293412 reaction equation
Cl[CH2:2][C:3]([N:5]1[C@@H:9]([CH3:10])[CH2:8][CH2:7][C@H:6]1[C:11]#[N:12])=[O:4].[CH:13]1([NH2:18])[CH2:17][CH2:16][CH2:15][CH2:14]1>C(#N)C>[CH:13]1([NH:18][CH2:2][C:3]([N:5]2[C@@H:9]([CH3:10])[CH2:8][CH2:7][C@H:6]2[C:11]#[N:12])=[O:4])[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 2906CyclopentylamineHCID 16090846(2S,5S)-1-(Chloroacetyl)-5-methylpyrrolidine-2-carbonitrile

Product 1

HCID 10243173HCID 10243173, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(2S,5S)-1-(2-Chloro-acetyl)-5-methyl-pyrrolidine-2-carbonitrile (50 mg, 0.30 mmol) and cyclopentylamine (0.059 mL, 0.6 mmol) were dissolved in acetonitrile (2 mL) and stirred overnight. The product was purified by reverse phase HPLC eluting with 0% to 70% acetonitrile/0.1% aqueous trifluoroacetic acid. 1H NMR (300 MHz, methanol-d4) δ ppm 1.36 (d, J=6.44 Hz, 3 H), 1.68 (m, 5 H), 1.85 (m, 3 H), 2.16 (m, 3 H), 2.38 (m, 3 H), 3.60 (m, 1 H), 4.20 (m, 1 H), 4.77 (m, 1 H). MS (ESI) m/z 236 (M+H)+.

Workup

  1. customThe product was purified by reverse phase HPLC
  2. washeluting with 0% to 70% acetonitrile/0.1% aqueous trifluoroacetic acid

Sources & evidence

ORD record
ord-26033e552ffa4519a4be19b3a7b5a040
Source dataset
uspto-grants-2007_07
Patent number
US07238724B2

Reaction notes

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