Hydroxylamine → HCID 178426453, compound

HRID 1010488Notes

Reaction equation

HRID 1010488 reaction equation
[C:1](/[N:3]=[C:4](\[N:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]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](OC)=[O:29])[CH2:6]1)#[N:2].[NH2:38][OH:39]>CO>[C:1](/[N:3]=[C:4](\[N:32]1[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]1)/[N:5]1[CH2:10][CH2:9][C@H:8]([C:11]([N:13]2[CH2:14][CH2:15][N:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][C:20]=3[CH3:27])[CH2:17][CH2:18]2)=[O:12])[C@@H:7]([C:28]([NH:38][OH:39])=[O:29])[CH2:6]1)#[N:2]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 178501356HCID 178501356, compound

Product 1

HCID 178426453HCID 178426453, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred solution of methyl (3R,4S)-1-[(E)-(cyanoimino)(piperidin-1-yl)methyl]-4-[4-(4-cyano-2-methylphenyl)piperazin-1-yl]carbonylpiperidine-3-carboxylate (53.30 mg, 0.0001054 mol) in anhydrous methanol (1.110 mL, 0.02740 mol) at rt was added the above 1.50 M of hydroxylamine in methanol (1.40 mL). The reaction mixture was stirred at rt for 2 h. LCMS showed the reaction was done. The reaction was quenched with saturated aqueous NH4Cl, extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by reverse phase HPLC with 5-95% MeCN/H2O to give the product. MS (ESI): (M+H)+=507.

Workup

  1. customThe reaction was quenched with saturated aqueous NH4Cl
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by reverse phase HPLC with 5-95% MeCN/H2O
  8. customto give the product

Sources & evidence

ORD record
ord-4affa1a614474c07b8e48dbfce6d081a
Source dataset
uspto-grants-2011_07
Patent number
US07973041B2

Reaction notes

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