1,2-Dichloroethane → HCID 86687196, compound

HRID 2285037Notes

Reaction equation

HRID 2285037 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH2:9])=[N:6][CH:7]=1.[CH3:10][N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]1[C:17](O)=[O:18].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.O.N>CN(C=O)C.CO.C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH:9][C:17]([C@@H:12]2[CH2:13][CH2:14][CH2:15][CH2:16][N:11]2[CH3:10])=[O:18])=[N:6][CH:7]=1

Participants

10

Reactant 6

HCID 111,2-DichloroethaneHCID 222AmmoniaHCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 6993266N-Methyl-L-pipecolic acidHCID 199167865-Fluoro-2-hydrazinylpyridine

Product 1

HCID 86687196HCID 86687196, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-fluoro-pyridin-2-yl)-hydrazine (250 mg, 1.96 mmol) in DMF (20.0 mL) was added (S)-1-methyl-piperidine-2-carboxylic acid (281 mg, 1.96 mmol), EDC (416 mg, 2.16 mmol) and HOBt.H2O (25.0 mg, 0.20 mmol). The reaction was stirred overnight then partitioned between EtOAc and water. The aqueous layer was then extracted with EtOAc (3×). The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated in vacuo. The residue was taken up in MeOH and loaded onto an SCX-2 cartridge, which was washed with MeOH. The product was eluted with 2M NH3 in MeOH; concentration in vacuo gave residue. FCC, using 0-10% [2M NH3 in MeOH] in DCM, gave the title compound (331 mg, 67%). LCMS (Method 1): Rt 0.35 min, m/z 253.2 [MH+].

Workup

  1. customthen partitioned between EtOAc and water
  2. extractionThe aqueous layer was then extracted with EtOAc (3×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. washwas washed with MeOH
  8. washThe product was eluted with 2M NH3 in MeOH
  9. concentrationconcentration in vacuo
  10. customgave residue

Sources & evidence

ORD record
ord-a4b36403b7ad406dab79f5031f5c05d8
Source dataset
uspto-grants-2015_09
Patent number
US09145413B2

Reaction notes

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