1,2-Dichloroethane → 1-[(6-Bromopyridin-2-yl)methyl]-N-methyl-1H-1,2,3-triazole-4-carboxamide

HRID 2060606노트

반응식

HRID 2060606 반응식
[Br:1][C:2]1[N:7]=[C:6]([CH2:8][N:9]2[CH:13]=[C:12]([C:14]([O-:16])=O)[N:11]=[N:10]2)[CH:5]=[CH:4][CH:3]=1.[K+].C1C=CC2N(O)N=[N:24][C:22]=2C=1.C(Cl)CCl.CN.Cl.CCN(C(C)C)C(C)C>CN(C=O)C.O>[Br:1][C:2]1[N:7]=[C:6]([CH2:8][N:9]2[CH:13]=[C:12]([C:14]([NH:24][CH3:22])=[O:16])[N:11]=[N:10]2)[CH:5]=[CH:4][CH:3]=1

참가 물질

8

반응물 5

HCID 111,2-Dichloroethane2회HCID 757711-Hydroxybenzotriazole2회HCID 81531DiisopropylethylamineHCID 6364545Methylamine hydrochloride2회HCID 86655085Potassium 1-[(6-bromopyridin-2-yl)methyl]-1,2,3-triazole-4-carboxylate

생성물 1

HCID 583352651-[(6-Bromopyridin-2-yl)methyl]-N-methyl-1H-1,2,3-triazole-4-carboxamide

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

Potassium 1-[(6-bromopyridin-2-yl)methyl]-1,2,3-triazole-4-carboxylate (450 mg, 1.40 mmol), HOBT (429 mg, 2.80 mmol), EDC (537 mg, 2.80 mmol), MeNH2.HCl (284 mg, 4.20 mmol), and DIEA (734 μL, 4.20 mmol) were combined in DMF (5.0 mL) and stirred at room temperature for 2 h. Additional HOBT (429 mg, 2.80 mmol), EDC (537 mg, 2.80 mmol), and MeNH2.HCl (284 mg, 4.20 mmol) were added to push the reaction to completion. After another 2 h at room temperature, the solution was diluted with water and extracted with 5:1 CH2Cl2:MeOH (3×). The combined organic layers were washed with brine, dried (MgSO4), and evaporated. Flash chromatography (0-10% MeOH/CH2Cl2) afforded the title compound as a colorless solid. LRMS (APCI) calc'd for C10H11BrN5O [M+H]+: 296, Found: 296.

후처리

  1. customthe reaction to completion
  2. waitAfter another 2 h at room temperature
  3. extractionextracted with 5:1 CH2Cl2
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated

출처 및 근거

ORD 기록
ord-76337240ce7744e68a6e01d612c2c598
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08278335B2

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