Acetonitrile → HCID 178501356, compound

HRID 535094Notes

Reaction equation

HRID 535094 reaction equation
[C:1](/[N:3]=[C:4](\OC1C=CC=CC=1)/[N:5]1[CH2:10][CH2:9][C@H:8]([C:11]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][C:20]=3[CH3:27])[CH2:15][CH2:14]2)=[O:12])[C@@H:7]([C:28]([O:30][CH3:31])=[O:29])[CH2:6]1)#[N:2].C(#N)C.[NH:42]1[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1>>[C:1](/[N:3]=[C:4](\[N:42]1[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1)/[N:5]1[CH2:10][CH2:9][C@H:8]([C:11]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][C:20]=3[CH3:27])[CH2:15][CH2:14]2)=[O:12])[C@@H:7]([C:28]([O:30][CH3:31])=[O:29])[CH2:6]1)#[N:2]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 8082PiperidineHCID 178501358HCID 178501358, compound

Product 1

HCID 178501356HCID 178501356, compound

Procedure

To a stirred solution of methyl (3R,4S)-1-[(Z)-(cyanoimino)(phenoxy)methyl]-4-[4-(4-cyano-2-methylphenyl)piperazin-1-yl]carbonylpiperidine-3-carboxylate (52 mg, 0.00010 mol) in acetonitrile (2.006 mL, 0.03840 mol) was added piperidine (0.200 mL, 0.00202 mol). The reaction mixture refluxed(oil bath at 85 deg). Upon completion reaction mixture concentrated in vacuum. The residue was purified by combiflash using 0-5% methanol/dichloromethane to give the product (53.3 mg, 98% in yield). MS (ESI): (M+H)+=506.

Workup

  1. customat 85 deg
  2. customUpon completion reaction mixture
  3. concentrationconcentrated in vacuum
  4. customThe residue was purified by combiflash
  5. customto give
  6. customthe product (53.3 mg, 98% in yield)

Sources & evidence

ORD record
ord-816652861cc042a3b82d398c3446ae54
Source dataset
uspto-grants-2014_10
Patent number
US08853243B2

Reaction notes

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