Water → 1-Hydroxybenzotriazole

HRID 630824ノート

反応式

HRID 630824 の反応式
[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

参加物

6

反応物 3

HCID 962WaterHCID 199167865-Fluoro-2-hydrazinylpyridineHCID 89623862HCID 89623862、化合物

生成物 1

HCID 757711-Hydroxybenzotriazole収率 260.9%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane触媒HCID 6228Dimethylformamide溶媒

実験手順

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+].

後処理

  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

出典と根拠

ORDレコード
ord-d334fa578f524403bb4eae1b17dd2a12
出典データセット
uspto-grants-2016_04
特許番号
US09315503B2

反応ノート

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