Water → 1-Hydroxybenzotriazole

HRID 630824노트

반응식

HRID 630824 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 757711-Hydroxybenzotriazole수율 260.9%

시약·촉매·용매 2

HCID 111,2-Dichloroethane촉매HCID 6228Dimethylformamide용매

실험 절차

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+].

후처리

  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

출처 및 근거

ORD 기록
ord-d334fa578f524403bb4eae1b17dd2a12
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315503B2

반응 노트

불러오는 중…