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

HRID 1807709Notes

Reaction equation

HRID 1807709 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.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

6

Reactant 4

HCID 8471TriethylamineHCID 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-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of tert-butyl piperazine-1-carboxylate (45.8 mmol, 8.53 g) and 4-(3-(cyclopropylmethyl)ureido)benzoic acid (45.8 mmol, 10.73 g) in dichloromethane (200 ml) was added triethylamine (103 mmol, 14.36 mL, 10.43 g) followed by 1-propane-phosphonic acid cyclic anhydride (68.7 mmol, 40.7 mL, 43.7 g; 50% solution in ethyl acetate). The reaction was stirred for 1 hour, then poured into saturated sodium hydrogen carbonate solution and extracted with dichloromethane. The organic phase was dried (magnesium sulfate), filtered and evaporated to a white solid (17.13 g)

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic phase was dried (magnesium sulfate)
  3. filtrationfiltered
  4. customevaporated to a white solid (17.13 g)

Sources & evidence

ORD record
ord-12d5a0ded7e3478fa779649a80b65107
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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