Triethylamine → HCID 66792810, compound

HRID 534954

Reaction equation

HRID 534954 reaction equation
Cl.Cl.[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)([CH3:6])([CH3:5])[CH3:4].[NH:19]1[C@@H:23]([C:24](O)=[O:25])[CH2:22][CH2:21][C:20]1=[O:27].C(N(CC)CC)C.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(#N)C>[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][N:16]([C:24]([C@@H:23]2[NH:19][C:20](=[O:27])[CH2:21][CH2:22]2)=[O:25])[CH2:15][CH2:14]1)([CH3:6])([CH3:4])[CH3:5]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 439685D-Pyroglutamic acidHCID 667511491-(2-Tert-butylphenyl)piperazine dihydrochloride

Product 1

HCID 66792810HCID 66792810, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(2-tert-butylphenyl)piperazine dihydrochloride obtained in Reference Example 1 (0.30 g, 1.03 mmol), (R)-(+)-2-pyrrolidone-5-carboxylic acid (0.15 g, 1.13 mmol), triethylamine (0.23 g, 2.26 mmol), EDCI (0.22 g, 1.13 mmol) and HOBt (0.17 g, 1.13 mmol) in acetonitrile (10 mL) was stirred at room temperature for 16 h. The reaction mixture was concentrated under reduced pressure and the resulting residue was partitioned between ethyl acetate and 10% sodium hydrogen carbonate solution. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting light pink solid was triturated with hexane to afford the title compound (0.32 g, 94%) as a light pink solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe resulting residue was partitioned between ethyl acetate and 10% sodium hydrogen carbonate solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting light pink solid was triturated with hexane

Sources & evidence

ORD record
ord-d543783a08754cd2b6be7c79c7753305
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Linked notes

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