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

HRID 408863Notes

Reaction equation

HRID 408863 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH:14]1([CH2:17][NH:18][C:19](=[O:30])[NH:20][C:21]2[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][CH:22]=2)[CH2:16][CH2:15]1.C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O.C(=O)([O-])O.[Na+]>ClCCl>[CH:14]1([CH2:17][NH:18][C:19](=[O:30])[NH:20][C:21]2[CH:22]=[CH:23][C:24]([C:25]([N:4]3[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]3)=[O:26])=[CH:28][CH:29]=2)[CH2:16][CH2:15]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 516892Sodium BicarbonateHCID 580558194-(3-(Cyclopropylmethyl)ureido)benzoic acid

Product 1

HCID 58055802tert-Butyl 4-(4-(3-(cyclopropylmethyl)ureido)benzoyl)piperazine-1-carboxylateYield 92.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl piperazine-1-carboxylate (45.8 mmol, 8.53 g) and 4-(3-(cyclopropylmethyl)ureido)benzoic acid (45.8 mmol, 10.73 g) were mixed in dichloromethane (200 mL) and triethylamine (103 mmol, 14.36 ml, 10.43 g) added followed by 1-propanephosphonic acid cyclic anhydride (68.7 mmol, 40.7 mL, 43.7 g, 50% solution in ethyl acetate). The reaction was stirred for 1 hour and then was poured into saturated sodium hydrogen carbonate solution and extracted with dichloromethane. The organic phase was dried (magnesium sulfate), filtered and concentrated under reduced pressure to give the title compound (17.13 g).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic phase was dried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0d29a74d9783495dbfe213a471e119e3
Source dataset
uspto-grants-2014_06
Patent number
US08759352B2

Reaction notes

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