(2S,5R)-1-(Chloroacetyl)-5-(prop-1-yn-1-yl)pyrrolidine-2-carbonitrile → HCID 10252297, compound

HRID 1293404Notes

Reaction equation

HRID 1293404 reaction equation
Cl[CH2:2][C:3]([N:5]1[C@@H:9]([C:10]#[C:11][CH3:12])[CH2:8][CH2:7][C@H:6]1[C:13]#[N:14])=[O:4].[F:15][C:16]([F:32])([F:31])[C:17]1[CH:30]=[CH:29][C:20]([O:21][CH:22]2[CH2:27][CH2:26][CH:25]([NH2:28])[CH2:24][CH2:23]2)=[CH:19][CH:18]=1>C(#N)C>[C:10]([C@@H:9]1[N:5]([C:3](=[O:4])[CH2:2][NH:28][CH:25]2[CH2:24][CH2:23][CH:22]([O:21][C:20]3[CH:29]=[CH:30][C:17]([C:16]([F:15])([F:31])[F:32])=[CH:18][CH:19]=3)[CH2:27][CH2:26]2)[C@H:6]([C:13]#[N:14])[CH2:7][CH2:8]1)#[C:11][CH3:12]

Participants

4

Reactant 2

HCID 16090855(2S,5R)-1-(Chloroacetyl)-5-(prop-1-yn-1-yl)pyrrolidine-2-carbonitrileHCID 18460866HCID 18460866, compound

Product 1

HCID 10252297HCID 10252297, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of (2S,5R)-1-(chloroacetyl)-5-propynylpyrrolidine-2-carbonitrile (0.030 g, 0.15 mmol, Example 88D) in acetonitrile (1 mL) at room temperature was added 4-(4-trifluoromethyl-phenoxy)-cyclohexylamine (79 mg, 0.31 mmol, Example 55A). The reaction mixture was stirred at room temperature for 18 hours, concentrated under reduced pressure and purified by flash chromatography with 3% methanol:dichloromethane to provide the titled compound. MS (ESI) m/z 434 (M+H)+; 1H NMR (DMSO) δ ppm 7.63 (d, 2H), 7.15 (d, 2H), 4.86 (m, 1H), 4.20-4.41 (m, 2H), 3.94 (m, 1H), 2.09-2.43 (m, 8H), 1.88 (d, 3H), 1.41-1.65 (m, 4H).

Workup

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

Sources & evidence

ORD record
ord-778d68dd76e6482fbd42ca518f4d0de9
Source dataset
uspto-grants-2007_07
Patent number
US07238724B2

Reaction notes

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