1,2-Dichloroethane → HCID 86687121, compound

HRID 2285111Notes

Reaction equation

HRID 2285111 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][CH:9]1[C:21]([OH:23])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:24][C:25]1[CH:26]=[CH:27][C:28]([NH:31][NH2:32])=[N:29][CH:30]=1.CCN(CC)CC.C1C=CC2N(O)N=NC=2C=1.O.C(Cl)CCl>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])[CH2:10][CH:9]1[C:21]([NH:32][NH:31][C:28]1[CH:27]=[CH:26][C:25]([F:24])=[CH:30][N:29]=1)=[O:23])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 962WaterHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 112559791,4-Di-Boc-piperazine-2-carboxylic acidHCID 199167865-Fluoro-2-hydrazinylpyridine

Product 1

HCID 86687121HCID 86687121, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of piperazine-1,2,4-tricarboxylic acid 1,4-di-tert-butyl ester (780 mg, 2.4 mmol) and (5-fluoro-pyridin-2-yl)-hydrazine (250 mg, 2.0 mmol) and Et3N (0.83 mL, 6 mmol) in DCM (20 mL) were added HOBt.H2O (27 mg, 0.2 mmol) and EDC (542 mg, 2.4 mmol) sequentially, and then the mixture stirred at RT overnight. The mixture was partitioned between EtOAc/water and extracted with EtOAc. The combined organics were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by FCC, using 0-10% MeOH in DCM, to give the title compound as a brown solid (550 mg, 63%). LCMS (Method 4): Rt 3.28, m/z 440 [MH+].

Workup

  1. customThe mixture was partitioned between EtOAc/water
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by FCC

Sources & evidence

ORD record
ord-950c0dd27b5d46038d8b4950f01b252f
Source dataset
uspto-grants-2015_09
Patent number
US09145413B2

Reaction notes

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