Triethylamine → N,N,1-trimethyl-1H-pyrazole-4-carboxamide

HRID 1802271노트

반응식

HRID 1802271 반응식
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]([OH:9])=O)[CH:4]=[N:3]1.[CH2:10]([N:12](CC)[CH2:13]C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.Cl.CNC>CN(C=O)C>[CH3:10][N:12]([CH3:13])[C:7]([C:5]1[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=1)=[O:9]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 6431601-Methyl-1H-pyrazole-4-carboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

생성물 1

HCID 59551573N,N,1-trimethyl-1H-pyrazole-4-carboxamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Methyl-1H-pyrazole-4-carboxylic acid (1.0 g, 7.93 mmol) was combined with DMF (10.0 ml) to give a light yellow solution. Triethylamine (3.3 ml, 23.8 mmol) and 2-(1H-benzo[d][1,2,3]triazol-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate (2.8 g, 8.72 mmol) were added. The reaction mixture was set under argon and stirred for 1 h at RT. Then dimethylamine hydrochloride (679 mg, 8.33 mmol) was added. The reaction mixture was stirred over night. The solvent was evaporated and the residue was absorbed on silica gel and chromatographed (amine silica gel cartridge, CH2Cl2). The resulting brown oil was dried at the HV over night. Yield: 1.16 g (96%); brown oil; MS: m/z=154.1 [M+H]+.

후처리

  1. customto give a light yellow solution
  2. stirringThe reaction mixture was stirred over night
  3. customThe solvent was evaporated
  4. customthe residue was absorbed on silica gel
  5. customchromatographed (amine silica gel cartridge, CH2Cl2)
  6. customThe resulting brown oil was dried at the HV over night

출처 및 근거

ORD 기록
ord-7052bce9aa1e439ca487024c77df2979
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08349824B2

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