1,2-Dichloroethane → HCID 86687131, compound

HRID 2282575Notes

Reaction equation

HRID 2282575 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH2:9])=[N:6][CH:7]=1.[C:10]([N:17]1[CH2:22][CH2:21][CH2:20][C@H:19]([C:23](O)=[O:24])[CH2:18]1)([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>C(Cl)Cl.CO.O>[C:13]([O:12][C:10]([N:17]1[CH2:22][CH2:21][CH2:20][C@H:19]([C:23]([NH:9][NH:8][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][N:6]=2)=[O:24])[CH2:18]1)=[O:11])([CH3:16])([CH3:15])[CH3:14]

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 6951168(3S)-1-((tert-butoxy)carbonyl)piperidine-3-carboxylic acidHCID 199167865-Fluoro-2-hydrazinylpyridine

Product 1

HCID 86687131HCID 86687131, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (5-fluoro-pyridin-2-yl)-hydrazine (1.27 g, 10.0 mmol), (S)-1-BOC piperidine-3-carboxylic acid (Alfa Aesar, 2.29 g, 10.0 mmol) and HOBt.H2O (153 mg, 1.00 mmol) in DCM (50 mL) was added EDC (2.30 g, 12.0 mmol) and the resulting orange solution stirred at RT for 16 h. Water (25 mL) was added and the mixture shaken. The aqueous was extracted with DCM (25 mL) then the combined organics were passed through a hydrophobic frit and concentrated in vacuo to leave a pale brown foam. FCC, using 0-5% MeOH in DCM, gave the title compound as a pale orange foam (3.21 g, 95%). LCMS (Method 3): Rt 3.14 min, m/z 361 [MNa+].

Workup

  1. stirringthe mixture shaken
  2. extractionThe aqueous was extracted with DCM (25 mL)
  3. concentrationconcentrated in vacuo
  4. customto leave a pale brown foam

Sources & evidence

ORD record
ord-017c85df9b164e858cb4ea652d0fe75a
Source dataset
uspto-grants-2015_09
Patent number
US09139584B2

Reaction notes

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