1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86702793, compound

HRID 1522909Notes

Reaction equation

HRID 1522909 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([NH2:12])=[O:11])=[CH:8][CH:7]=1)=[O:4].[NH:15]1[CH2:20][CH2:19][CH:18]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:17][CH2:16]1.C1CCN2C(=NCCC2)CC1>C(#N)C>[C:10]([C:9]1[CH:13]=[CH:14][C:6]([NH:5][C:3](=[O:4])[CH2:2][N:15]2[CH2:16][CH2:17][CH:18]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:25])[CH3:27])[CH2:19][CH2:20]2)=[CH:7][CH:8]=1)(=[O:11])[NH2:12]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 7238334-(N-Boc-amino)piperidineHCID 23166884-[(chloroacetyl)amino]benzamide

Product 1

HCID 86702793HCID 86702793, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-(2-chloroacetamido)benzamide (0.57 g; 2.68 mmol), tert-butyl piperidin-4-ylcarbamate (0.55 g; 2.68 mmol) and DBU (0.40 mL; 2.68 mmol) in ACN (30 mL) is stirred at r.t. over night. Then the solvent is evaporated and the residue is dissolved in DCM. The solution is washed once with water, then with brine. The organic layer is dried and the solvent is evaporated. The residue is suspended in ether, filtered off with suction and dried to yield tert-butyl 1-(2-(4-carbamoylphenylamino)-2-oxoethyl)piperidin-4-ylcarbamate.

Workup

  1. customThen the solvent is evaporated
  2. dissolutionthe residue is dissolved in DCM
  3. washThe solution is washed once with water
  4. customThe organic layer is dried
  5. customthe solvent is evaporated
  6. filtrationfiltered off with suction
  7. customdried

Sources & evidence

ORD record
ord-72d54b5a47384f08af933f069dc79c8c
Source dataset
uspto-grants-2015_07
Patent number
US09078909B2

Reaction notes

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