Diisopropylethylamine → HCID 57917715, compound

HRID 1878380Notes

Reaction equation

HRID 1878380 reaction equation
[CH3:1][C@@H:2]1[NH:7][C@H:6]([CH3:8])[CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1.[C:16]([NH:20][C:21](=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28]Cl)[CH:23]=1)([CH3:19])([CH3:18])[CH3:17].C(N(C(C)C)C(C)C)C>O1CCCC1.ClCCl>[C:16]([NH:20][C:21]([C:22]1[CH:23]=[C:24]([CH:25]=[CH:26][CH:27]=1)[CH2:28][N:7]1[C@H:2]([CH3:1])[CH2:3][N:4]([C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])[CH2:5][C@@H:6]1[CH3:8])=[O:30])([CH3:19])([CH3:17])[CH3:18]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 10822535tert-butyl (3R,5S)-3,5-dimethylpiperazine-1-carboxylateHCID 43156221N-tert-butyl-3-(chloromethyl)benzamide

Product 1

HCID 57917715HCID 57917715, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3S,5R)-tert-butyl 3,5-dimethylpiperazine-1-carboxylate (0.05 g, 0.23 mmol) and N-tert-butyl-3-(chloromethyl)benzamide (0.052 g, 0.23 mmol) in tetrahydrofuran (2 mL) was added N-ethyl-N-isopropylpropan-2-amine (0.080 mL, 0.46 mmol). The resultant mixture was stirred at 80° C. for 16 hours. The mixture was cooled to room temperature, diluted with dichloromethane (50 mL) and washed with saturated ammonium chloride (aqueous) and brine. The organic phase was dried (sodium sulfate), filtered and concentrated under vacuum. The crude material was purified by column chromatography on silica (using a solvent gradient of dichloromethane/ethyl acetate) to afford the title compound (0.070 g) as a white solid.

Workup

  1. washwashed with saturated ammonium chloride (aqueous) and brine
  2. dry with materialThe organic phase was dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe crude material was purified by column chromatography on silica (

Sources & evidence

ORD record
ord-8f5f0e2b3dfd46679ba48f2f115dcf9f
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

Loading…