HCID 7183144, compound → HCID 24860010, compound

HRID 855839Notes

Reaction equation

HRID 855839 reaction equation
Cl[CH2:2][C:3]([N:5]1[C@@H:9]([C:10]#[C:11]C)[CH2:8][CH2:7][C@H:6]1[C:13]#[N:14])=[O:4].[NH2:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)=[O:23])[CH2:18][CH2:17]1>C(#N)C>[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([C:22]([N:19]2[CH2:18][CH2:17][CH:16]([NH:15][CH2:2][C:3]([N:5]3[C@@H:9]([C:10]#[CH:11])[CH2:8][CH2:7][C@H:6]3[C:13]#[N:14])=[O:4])[CH2:21][CH2:20]2)=[O:23])=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 7183144HCID 7183144, compoundHCID 16090855(2S,5R)-1-(Chloroacetyl)-5-(prop-1-yn-1-yl)pyrrolidine-2-carbonitrile

Product 1

HCID 24860010HCID 24860010, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of (2S,5R)-1-(chloroacetyl)-5-propynylpyrrolidine-2-carbonitrile (0.023 g, 0.118 mmol, Example 8D) in acetonitrile (1 mL) at room temperature was added (4-amino-piperidin-1-yl)-(4-chloro-phenyl)methanone (56 mg, 0.235 mmol). 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 399 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-66dac578c2074a2594c7c0a6634da1d8
Source dataset
uspto-grants-2007_08
Patent number
US07262207B2

Reaction notes

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