1,2-Dichloroethane → HCID 86687143, compound

HRID 630854Notes

Reaction equation

HRID 630854 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH2:9])=[N:6][CH:7]=1.[F:10][C@H:11]1[CH2:15][N:14]([CH3:16])[C@H:13]([C:17](O)=[O:18])[CH2:12]1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>C(Cl)Cl.CN(C=O)C.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH:9][C:17]([C@@H:13]2[CH2:12][C@@H:11]([F:10])[CH2:15][N:14]2[CH3:16])=[O:18])=[N:6][CH:7]=1

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 199167865-Fluoro-2-hydrazinylpyridineHCID 55300764(4R)-4-Fluoro-1-methyl-L-proline

Product 1

HCID 86687143HCID 86687143, compoundYield 47.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of (5-fluoro-pyridin-2-yl)-hydrazine (378 mg, 2.98 mmol), Intermediate 91a (600 mg, 4.08 mmol) and HOBt.H2O (44 mg, 0.12 mmol) in DCM (10 mL) and DMF (3 mL) was added EDC (628 mg, 3.28 mmol) portionwise at RT and the mixture stirred at RT for 17 h. The solution was diluted with water and extracted with DCM. The combined organics were dried and concentrated in vacuo. The residue was purified by FCC, using 0-7.5% [2M NH3 in MeOH] in DCM, to give the title compound as light orange powder (366 mg, 35%). LCMS (Method 3): Rt 0.56 min, m/z 257 [MH+].

Workup

  1. extractionextracted with DCM
  2. customThe combined organics were dried
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by FCC

Sources & evidence

ORD record
ord-3a2bef8675094ee582efc35ebcbf24a5
Source dataset
uspto-grants-2016_04
Patent number
US09315503B2

Reaction notes

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