1-Hydroxybenzotriazole → 4-{4-[(4'-Isopropyl-5-methyl-biphenyl-2-carbonyl)-amino]-phenyl}piperazine-1-carboxylic Acid Tert-Butyl Ester

HRID 1267114Notes

Reaction equation

HRID 1267114 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:21]([C:24]1[CH:29]=[CH:28][C:27]([C:30]2[C:31]([C:37](O)=[O:38])=[CH:32][CH:33]=[C:34]([CH3:36])[CH:35]=2)=[CH:26][CH:25]=1)([CH3:23])[CH3:22].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl.CCN(CC)CC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][C:17]([NH:20][C:37]([C:31]3[C:30]([C:27]4[CH:28]=[CH:29][C:24]([CH:21]([CH3:23])[CH3:22])=[CH:25][CH:26]=4)=[CH:35][C:34]([CH3:36])=[CH:33][CH:32]=3)=[O:38])=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11011301tert-Butyl 4-(4-aminophenyl)piperazine-1-carboxylateHCID 185454504'-Isopropyl-5-methyl-biphenyl-2-carboxylic acid

Product 1

HCID 540547824-{4-[(4'-Isopropyl-5-methyl-biphenyl-2-carbonyl)-amino]-phenyl}piperazine-1-carboxylic Acid Tert-Butyl EsterYield 52%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a stirred solution of 4-(4-amino-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (4.15 g), 4′-isopropyl-5-methyl-biphenyl-2-carboxylic acid (3.81 g), HOBt (2.36 g), and Et3N (1.97 g) in CH2Cl2 (50 mL) was added EDCl (3.72 g) and the mixture was stirred at room temperature for 16 hours. The organic solution was then washed with water, with a saturated solution of NaHCO3, with brine and dried over Na2SO4. After filtration and evaporation of the filtrate, the residue was crystallized from diisopropyl ether to give the title compound (4 g) as white crystals.

Workup

  1. washThe organic solution was then washed with water, with a saturated solution of NaHCO3, with brine
  2. dry with materialdried over Na2SO4
  3. filtrationAfter filtration and evaporation of the filtrate
  4. customthe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-4274c771fc4745b58400d346d47c7789
Source dataset
uspto-grants-2003_04
Patent number
US06552022B1

Reaction notes

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