Water → 1-Hydroxybenzotriazole

HRID 2285096Notes

Reaction equation

HRID 2285096 reaction equation
[OH2:1].F[C:3]1[CH:4]=[CH:5][C:6]([NH:9][NH2:10])=N[CH:8]=1.C(OC(C[CH2:19][N:20]1CCC[C@H]1C(O)=O)=O)(C)(C)C>CN(C=O)C.C(Cl)CCl>[CH:3]1[CH:4]=[CH:5][C:6]2[N:9]([OH:1])[N:10]=[N:20][C:19]=2[CH:8]=1

Participants

6

Reactant 3

HCID 962WaterHCID 199167865-Fluoro-2-hydrazinylpyridineHCID 89623862HCID 89623862, compound

Product 1

HCID 757711-HydroxybenzotriazoleYield 260.9%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneCatalystHCID 6228DimethylformamideSolvent

Procedure

H2O (695 mg, 3.62 mmol) was added to a suspension of (5-fluoro-pyridin-2-yl)-hydrazine (418 mg, 3.29 mmol), Intermediate 84b (840 mg, 3.29 mmol), and EDC (44.0 mg, 0.33 mmol) in DMF (25.0 mL). 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 purified by FCC, using 0-10% [2M NH3 in MeOH] in DCM, to give the title compound (1.16 g, 99%). LCMS (Method 1): Rt 2.06 mins, m/z 353.3 [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. customThe residue was purified by FCC

Sources & evidence

ORD record
ord-fa78d6eef1434a9d842907d962b23d25
Source dataset
uspto-grants-2015_09
Patent number
US09145413B2

Reaction notes

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