Triethylamine → tert-Butyl 4-(4-(3-cyclobutylureido)benzoyl)piperazine-1-carboxylate

HRID 1878413Notes

Reaction equation

HRID 1878413 reaction equation
[CH:1]1([NH:5][C:6](=[O:17])[NH:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[N:25]1([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>[Cl-].[Na+].O.O.ClCCl>[CH:1]1([NH:5][C:6](=[O:17])[NH:7][C:8]2[CH:9]=[CH:10][C:11]([C:12]([N:28]3[CH2:27][CH2:26][N:25]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:30][CH2:29]3)=[O:14])=[CH:15][CH:16]=2)[CH2:2][CH2:3][CH2:4]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 624152074-(3-Cyclobutylureido)benzoic acid

Product 1

HCID 57917609tert-Butyl 4-(4-(3-cyclobutylureido)benzoyl)piperazine-1-carboxylateYield 94.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A flask was charged with 4-(3-cyclobutylureido)benzoic acid (51.3 mmol, 12.023 g), triethyl-amine (129 mmol, 18 mL, 13.07 g) and dichloromethane (75 mL) and cooled to 0° C. tert-Butyl piperazine-1-carboxylate (51.3 mmol, 9.56 g) was then added and the reagents were stirred together for 10 minutes at 0° C. before 1-propanephosphonic acid cyclic anhydride (64.2 mmol, 38.0 mL, 40.8 g, 50% solution in ethyl acetate) was slowly added. The reaction mixture was allowed to warm slowly to room temperature. After 5 hours stirring, the reaction was poured into a flask containing water (100 mL) and brine (20 ml). The mixture was then stirred and left to stand overnight. The resulting precipitate was collected by vacuum filtration, washed with cold water and dried under vacuum to yield the title compound as a white powder (19.6 g). MS (ESI) m/z 403.5 [M+H]+

Workup

  1. additionwas then added
  2. additionwas slowly added
  3. additionthe reaction was poured into a flask
  4. stirringThe mixture was then stirred
  5. waitleft
  6. waitto stand overnight
  7. filtrationThe resulting precipitate was collected by vacuum filtration
  8. washwashed with cold water
  9. customdried under vacuum

Sources & evidence

ORD record
ord-96a7b8f6adc84f91bc60b149c6a545da
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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