Benzyl succinimido carbonate → HCID 10268846, compound

HRID 1827157Notes

Reaction equation

HRID 1827157 reaction equation
[CH3:1][C:2]1[C:3]([NH:8][CH2:9][CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[N:4][CH:5]=[N:6][CH:7]=1.O=C1CCC(=O)N1[O:23][C:24](=O)[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C=O)C>[CH2:26]([O:25][C:24]([N:13]1[CH2:14][CH2:15][CH:10]([CH2:9][NH:8][C:3]2[C:2]([CH3:1])=[CH:7][N:6]=[CH:5][N:4]=2)[CH2:11][CH2:12]1)=[O:23])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 83172Benzyl succinimido carbonateHCID 22135665HCID 22135665, compound

Product 1

HCID 10268846HCID 10268846, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-[(5-methyl-pyrimidin-4-ylamino)-methyl]-piperidine (0.20 g, 0.97 mmol), in DMF (3 mL) was added carbonic acid benzyl ester 2,5-dioxo-pyrrolidin-1-yl ester (0.24 g, 0.97 mmol). The resulting reaction solution was stirred at rt for 0.5 h, then concentrated in vacuo. The residue was purified by silica gel chromatography (1-10 (10% NH4OH in MeOH)/99-90 CH2Cl2) to give 4-[(5-methyl-pyrimidin-4-ylamino)-methyl]-piperidine-1-carboxylic acid benzyl ester.

Workup

  1. customThe resulting reaction solution
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by silica gel chromatography (1-10 (10% NH4OH in MeOH)/99-90 CH2Cl2)

Sources & evidence

ORD record
ord-e3aa8cc2dc554fe8b816966db58b048b
Source dataset
uspto-grants-2006_05
Patent number
US07053089B2

Reaction notes

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