1-Methyl-4-piperidone → HCID 66754888, compound

HRID 1643980Notes

Reaction equation

HRID 1643980 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7](=[O:38])[CH:8]([N:15]2[C:19]3[CH:20]=[C:21]([C:24]#[N:25])[CH:22]=[CH:23][C:18]=3[N:17]([S:26]([C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)(=[O:28])=[O:27])[C:16]2=[O:37])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:3]1.[CH3:39][N:40]1[CH2:45][CH2:44][C:43](=O)[CH2:42][CH2:41]1>C1COCC1>[CH3:36][O:35][C:32]1[CH:31]=[CH:30][C:29]([S:26]([N:17]2[C:18]3[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][C:19]=3[N:15]([CH:8]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:7]([N:4]3[CH2:5][CH2:6][C@H:2]([NH:1][CH:43]4[CH2:44][CH2:45][N:40]([CH3:39])[CH2:41][CH2:42]4)[CH2:3]3)=[O:38])[C:16]2=[O:37])(=[O:27])=[O:28])=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 740491-Methyl-4-piperidoneHCID 66754653HCID 66754653, compound

Product 1

HCID 66754888HCID 66754888, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[2-((S)-3-amino-pyrrolidin-1-yl)-2-oxo-1-phenyl-ethyl]-1-(4-methoxy-benzenesulfonyl)-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carbonitrile (Example 171, 200 mg, 0.38 mmol) and 1-methyl-4-piperidone (0.087 mL, 0.75 mmol) in THF (5 mL) MP-(OAc)3BH resin (Argonaut; 2.55 mmol/g; 369 mg, 0.94 mmol) was added. The reaction mixture was agitated at room temperature for 24 hours, then filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel using 15% methanol in CH2Cl2 to afford 1-(4-methoxy-benzenesulfonyl)-3-{2-[(S)-3-(1-methyl-piperidin-4-ylamino)-pyrrolidin-1-yl]-2-oxo-1-phenyl-ethyl}-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carbonitrile (167 mg, 71%) as a white solid.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash chromatography on silica gel using 15% methanol in CH2Cl2

Sources & evidence

ORD record
ord-5b8a01365cfe424ba6ae540f30d83e3c
Source dataset
uspto-grants-2012_02
Patent number
US08119676B2

Reaction notes

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