Diisopropylethylamine → HCID 46867020, compound

HRID 416887

Reaction equation

HRID 416887 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([CH:8]([CH3:10])[CH3:9])[O:6][CH:7]=1.CCN(C(C)C)C(C)C.[C:20]([N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]>C(Cl)Cl.CCOC(C)=O>[CH:8]([C:5]1[O:6][CH:7]=[C:3]([CH2:2][N:30]2[CH2:29][CH2:28][N:27]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:32][CH2:31]2)[N:4]=1)([CH3:10])[CH3:9]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27632914-(Chloromethyl)-2-(propan-2-yl)-1,3-oxazole

Product 1

HCID 46867020HCID 46867020, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
35 °C

Procedure

4-(Chloromethyl)-2-isopropyloxazole (0.920 g, 5.75 mmol, 1 eq) was suspended in DCM (9 mL). DIPEA (2.5 mL, 14.4 mmol, 2.5 eq) was added dropwise, followed by N-Boc-piperazine (2.350 g, 12.6 mmol, 2.2 eq). The reaction mixture was stirred at 35° C. for 17 h, then diluted with EtOAc, washed with H2O, and brine. The organic layer was separated, dried (MgSO4) and the solvent removed in vacuo. The crude product was purified by column chromatography on a Biotage SP1 system (DCM/EtOAc; v/v 1:1) to give the title compound (1.760 g, 99%); 1H-NMR (500 MHz, CDCl3): δ 1.33 (d, J=5.5 Hz, 6H, iPr—CH3), 1.45 (s, 9H, C(CH3)3), 2.45 (br t, J=4.8 Hz, 4H, piperazine N(CH2)2), 3.07 (m, 1H, iPr—CH), 3.41-3.50 (m, 6H, piperazine N(CH2)2 and NCH2), 7.41 (s, 1H, oxazole 5-H); LC (Method B)-MS (ESI, m/z): Rt=2.51 min—310 [(M+H)+, 100%].

Workup

  1. washwashed with H2O, and brine
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customThe crude product was purified by column chromatography on a Biotage SP1 system (DCM/EtOAc; v/v 1:1)

Sources & evidence

ORD record
ord-f5b8115fff534e14913fab0c94b18b51
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Linked notes

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