(2S,5R)-1-(2-chloroacetyl)-5-ethynylpyrrolidine-2-carbonitrile → HCID 178455775, compound

HRID 475383Notes

Reaction equation

HRID 475383 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].[C:14]([O:18][C:19](=[O:34])[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH:27]2[CH2:32][CH2:31][CH:30]([NH2:33])[CH2:29][CH2:28]2)=[CH:22][CH:21]=1)([CH3:17])([CH3:16])[CH3:15]>C(#N)C>[C:14]([O:18][C:19](=[O:34])[C:20]1[CH:25]=[CH:24][C:23]([O:26][C@H:27]2[CH2:28][CH2:29][C@H:30]([NH:33][CH2:2][C:3]([N:5]3[C@@H:9]([C:10]#[CH:11])[CH2:8][CH2:7][C@H:6]3[C:12]#[N:13])=[O:4])[CH2:31][CH2:32]2)=[CH:22][CH:21]=1)([CH3:17])([CH3:15])[CH3:16]

Participants

4

Reactant 2

HCID 16090854(2S,5R)-1-(2-chloroacetyl)-5-ethynylpyrrolidine-2-carbonitrileHCID 667566814-(4-Aminocyclohexyloxy)-benzoic acid tert-butyl ester

Product 1

HCID 178455775HCID 178455775, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of (2S,5R)-1-(chloroacetyl)-5-ethynylpyrrolidine-2-carbonitrile (0.03 g, 0.15 mmol, Example 8D) in acetonitrile (1 mL) at room temperature was added 4-(4-aminocyclohexyloxy)-benzoic acid tert-butyl ester (89 mg, 0.31 mmol). The reaction mixture was stirred at room temperature for 18 hours, concentrated under reduced pressure and purified by flash chromatography with 3% methanol/97% dichloromethane to provide the titled compound. MS (ESI) m/z 452 (M+H)+; 1H NMR (CDCl3) δ 7.91 (d, 2H), 6.86 (d, 2H), 4.74 (m, 1H), 4.60 (m, 1H), 4.28 (m, 1H), 3.64 (m, 2H), 2.32-2.59 (m, 6H), 2.17 (m, 2H), 2.04 (m, 2H), 1.24-1.54 (m, 4H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified by flash chromatography with 3% methanol/97% dichloromethane

Sources & evidence

ORD record
ord-caff3a251cf44d12ad792ea9866f9349
Source dataset
uspto-grants-2014_01
Patent number
US08637546B2

Reaction notes

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