1-Bromopropane → N-(8-propyl-8-azabicyclo[3.2.1]oct-3-yl)-4-methyl-1H-indazol-5-amine

HRID 1269878노트

반응식

HRID 1269878 반응식
C(=O)([O-])[O-].[K+].[K+].[CH3:7][CH2:8][CH2:9]Br.[CH:11]12[NH:18][CH:15]([CH2:16][CH2:17]1)[CH2:14][CH:13]([NH:19][C:20]1[C:21]([CH3:29])=[C:22]3[C:26](=[CH:27][CH:28]=1)[NH:25][N:24]=[CH:23]3)[CH2:12]2>CN(C)C=O>[CH2:9]([N:18]1[CH:15]2[CH2:16][CH2:17][CH:11]1[CH2:12][CH:13]([NH:19][C:20]1[C:21]([CH3:29])=[C:22]3[C:26](=[CH:27][CH:28]=1)[NH:25][N:24]=[CH:23]3)[CH2:14]2)[CH2:8][CH3:7]

참가 물질

5

반응물 3

HCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 18447427N-(8-azabicyclo[3.2.1]oct-3-yl)-4-methyl-1H-indazol-5-amine

생성물 1

HCID 18447447N-(8-propyl-8-azabicyclo[3.2.1]oct-3-yl)-4-methyl-1H-indazol-5-amine수율 42%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Potassium carbonate (122 mg, 0.883 mmol) and then n-propyl bromide (40 μl, 0.440 mmol) were added to a solution of the N-(8-azabicyclo[3.2.1]oct-3-yl)-4-methyl-1H-indazol-5-amine (74 mg, 0.289 mmol) obtained in Example 501 in N,N-dimethylformamide (2 ml), and the resulting mixture was stirred at room temperature for 15 hours. After the solid was removed by filtration, the solvent was distilled off under reduced pressure as an azeotrope with toluene. The residue was purified by a silica gel column chromatography (chloroform/methanol/triethylamine=100/1/5) and then a preparative thin-layer chromatography (200×200×0.5 mm, 2 plates, eluent: chloroform/methanol/triethylamine=100/5/5) to obtain N-(8-propyl-8-azabicyclo[3.2.1]oct-3-yl)-4-methyl-1H-indazol-5-amine (36 mg, 42%).

후처리

  1. customAfter the solid was removed by filtration
  2. distillationthe solvent was distilled off under reduced pressure as an azeotrope with toluene
  3. customThe residue was purified by a silica gel column chromatography (chloroform/methanol/triethylamine=100/1/5)

출처 및 근거

ORD 기록
ord-72a699e993934173912506aad9c70152
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199147B2

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