4-Methylmorpholine → HCID 53776755, compound

HRID 392513Notes

Reaction equation

HRID 392513 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][C@@H:9]1[C:21]([O-:23])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:24]1([CH2:29][CH2:30][CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][NH:32]2)[CH:28]=[CH:27][N:26]=[CH:25]1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C=O)C>[N:24]1([CH2:29][CH2:30][CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][N:32]2[C:21]([C@H:9]2[CH2:10][N:11]([C:14]([O:16][C:17]([CH3:19])([CH3:20])[CH3:18])=[O:15])[CH2:12][CH2:13][N:8]2[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:23])[CH:28]=[CH:27][N:26]=[CH:25]1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 226629092-[2-(1H-Imidazol-1-yl)ethyl]piperidineHCID 263395011,2,4-Piperazinetricarboxylic acid, 1,4-bis(1,1-dimethylethyl) ester, (2R)-

Product 1

HCID 53776755HCID 53776755, compoundYield 30.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

1,4-Di-N-tert-butoxycarbonylpiperazine-2(R)-carboxylate (prepared as described in Preparative Example 2) (0.6946 g, 2.1 mmoles), 2(R/S)-[2-(1H-imidazol-1-yl)ethyl]piperidine (0.49 g, 2.73 mmoles) (prepared as described in Preparative Example 57, Step D) (INO972), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.524 g, 2.73 mmoles), 1-hydroxybenzotriazole (0.3693 g, 2.73 mmoles) and 4-methylmorpholine (0.2765 g, 0.3005 mL, 2.73 mmoles) were dissolved in anhydrous DMF (3 mL) and the mixture was stirred under argon at 25° C. for 122 h. The mixture was evaporated to dryness and chromatographed on silica gel using 2-3%(10% conc. ammonium hydroxide in methanol)-dichloromethane as the eluant to give the title compound (0.3127 g, 30%): CIMS: m/z 492.4 (MH+); δH (CDCl3) 1.47 (18H, s, CH3), 7.01 (1H, s, Im-H5), 7.05 (1H, s, Im-H4) and 7.63 ppm (1H, s, Im-H2); δC (CDCl3) CH3: 28.2, 28.2, 28.2, 28.4, 28.4, 28.4; CH2: 19.1, 25.9, 26.2, 31.9, 40.8/41.3, 41.7, 43.0, 44.0; CH: 46.0, ˜52.1, 128.4, 137.2; C: ˜80.4, 80.6, ˜154.3, ˜154.3 and ˜169.8.

Workup

  1. customThe mixture was evaporated to dryness
  2. customchromatographed on silica gel using 2-3%(10% conc. ammonium hydroxide in methanol)-dichloromethane as the eluant

Sources & evidence

ORD record
ord-e175b19bfebe4e228e9dba70577df872
Source dataset
uspto-grants-2004_10
Patent number
US06800636B2

Reaction notes

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