Triethylamine → HCID 18536043, compound

HRID 412178Notes

Reaction equation

HRID 412178 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[C:16]2[C:19](O)=[O:20])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C=O)C>[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][N:32]([C:19]([C:16]2[C:17]3[C:12](=[CH:11][CH:10]=[C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH:18]=3)[CH:13]=[CH:14][CH:15]=2)=[O:20])[CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:23])[CH3:24]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18536057HCID 18536057, compound

Product 1

HCID 18536043HCID 18536043, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the product from Step C (3.58 mmol), N-tert-butoxycarbonylpiperazine (733 mg, 3.93 mmol), EDC hydrochloride (750 mg, 3.93 mmol), HOBT (483 mg, 3.58 mmol), and triethylamine (0.498 mL, 3.58 mmol) were stirred in dry DMF (15 mL) at room temperature for two days. After concentration in vacuo, the residue was partitioned between EtOAc and 50% NaHCO3 solution, washed with water and brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (30% EtOAc/hexane) to yield the desired product as a white foam.

Workup

  1. concentrationAfter concentration in vacuo
  2. customthe residue was partitioned between EtOAc and 50% NaHCO3 solution
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel (30% EtOAc/hexane)

Sources & evidence

ORD record
ord-e07a82571ec546a7a27e87462c4e3616
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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