Water → 1-Hydroxybenzotriazole

HRID 1402263Notes

Reaction equation

HRID 1402263 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-a82ee40e830d4cdd9bc4fea329d3397c
Source dataset
uspto-grants-2014_12
Patent number
US08907094B2

Reaction notes

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