1,1'-Carbonyldiimidazole → HCID 25221225, compound

HRID 1642484Notes

Reaction equation

HRID 1642484 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2([CH3:25])[CH2:19][CH2:18][N:17]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:16]2)[CH2:11][CH2:10]1.[C:26](N1C=CN=C1)(N1C=CN=C1)=[O:27]>C(#N)C>[CH3:25][C:15]1([N:12]2[CH2:13][CH2:14][CH:9]([N:8]3[C@H:3]4[CH2:4][CH2:5][CH2:6][CH2:7][C@@H:2]4[NH:1][C:26]3=[O:27])[CH2:10][CH2:11]2)[CH2:19][CH2:18][N:17]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:16]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 57619822Ethyl 3-[4-[[(1S,2S)-2-aminocyclohexyl]amino]-1-piperidinyl]-3-methyl-1-pyrrolidinecarboxylate

Product 1

HCID 25221225HCID 25221225, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of ethyl 3-[4-[[(1S,2S)-2-aminocyclohexyl]amino]-1-piperidyl]-3-methyl-pyrrolidine-1-carboxylate (600 mg, 1.70 mmol) in anhydrous acetonitrile (30 mL) was added with 1,1′-carbonyldiimidazole (551.92 mg, 3.40 mmol) and stirred at room temperature for 12 h. The solvent was removed in vacuo; the residue was dissolved in dichloromethane (60 mL), washed with water and brine and dried over anhydrous MgSO4. Concentrated in vacuo and the residue was purified by flash chromatography (dichloromethane/methanol) to afford the title compound as a white solid (45 mg). 1H NMR (CD3OD, 400 MHz): δ 4.15 (q, 2H), 3.62-3.51 (m, 2H), 2.41 (m, 2H), 3.22 (m, 1H), 3.19 (brd, 1H), 2.99 (m, 3H), 2.76 (brs, 1H), 2.45 (m, 3H), 2.01-1.82 (m, 6H), 1.74 (brd, 1H), 1.65 (brd, 1H), 1.45 (m, 4H), 1.25 (t, 3H), 1.12 (s, 3H). MS (M+1): 379.18.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in dichloromethane (60 mL)
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationConcentrated in vacuo
  6. customthe residue was purified by flash chromatography (dichloromethane/methanol)

Sources & evidence

ORD record
ord-56231d6830b242468801ea9b79f482a0
Source dataset
uspto-grants-2012_02
Patent number
US08119661B2

Reaction notes

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