Diisopropylethylamine → HCID 46743071, compound

HRID 416862Notes

Reaction equation

HRID 416862 reaction equation
Cl[CH2:2][C:3]1[C:4]([CH3:9])=[N:5][O:6][C:7]=1[CH3:8].[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:9][C:4]1[C:3]([CH2:2][N:20]2[CH2:19][CH2:18][N:17]([C:15]([O:14][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:16])[CH2:22][CH2:21]2)=[C:7]([CH3:8])[O:6][N:5]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 88246Isoxazole, 4-(chloromethyl)-3,5-dimethyl-HCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 46743071HCID 46743071, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
35 °C

Procedure

A solution of 4-chloromethyl-3,5-dimethylisoxazole (100 mg, 0.69 mmol) in CH2Cl2 (4 mL) was treated with tert-butyl-1-piperazine carboxylate (2.5 eq, 1.71 mmol, 320 mg) and iPr2NEt (3.0 eq, 2.06 mmol, 0.36 mL) and stirred at 35° C. for 8 h. Concentration in vacuo and preparative tlc purification (EtOAc) gave the desired product (111 mg, 55%) as a colourless solid; δH (500 MHz, DMSO-d6) 1.39 (s, 9H, C(CH3)3), 2.17 (s, 3H, CH3), 2.28 (t, J=4.5 Hz, 4H, piperazine N(CH2)2), 2.31 (s, 3H, CH3), 3.23 (s, 2H, NCH2), 3.30 (hidden by DMSO peak, 4H, piperazine N(CH2)2);

Workup

  1. concentrationConcentration
  2. customin vacuo and preparative tlc purification (EtOAc)

Sources & evidence

ORD record
ord-7ce07c92522543c8bfea68c7661500a9
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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