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

HRID 1269878ノート

反応式

HRID 1269878 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-72a699e993934173912506aad9c70152
出典データセット
uspto-grants-2007_04
特許番号
US07199147B2

反応ノート

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