4-Methoxybenzylamine → 3-[(1-Amino-5-isoquinolyl)oxy]propylamine hydrochloride

HRID 10502

反応式

HRID 10502 の反応式
C(OC([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[CH:15]=[CH:16][N:17]=[C:18]2[Cl:23])=O)(C)(C)C.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.COC1C=CC(C[NH2:52])=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C>[ClH:23].[NH2:52][C:18]1[C:19]2[C:14](=[C:13]([O:12][CH2:11][CH2:10][CH2:9][NH2:8])[CH:22]=[CH:21][CH:20]=2)[CH:15]=[CH:16][N:17]=1

参加物

8

反応物 4

HCID 754524-MethoxybenzylamineHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 21979957N-(tert-butoxycarbonyl)-3-[(1-chloro-5-isoquinolyl)oxy]propylamine2 回HCID 23676156Sodium t-butoxide

生成物 1

HCID 219798583-[(1-Amino-5-isoquinolyl)oxy]propylamine hydrochloride

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

The title compound was synthesized from Intermediate 18 according to the method described in a reference (Buchwald, S. L., J. Org. Chem., 65, 1158 (2000)). That is, a suspension of Intermediate 18 (674 mg), tris (dibenzylideneacetone)dipalladium(0) (92 mg, Aldrich), 2-(di-tert-butylphosphino)biphenyl (119 mg, Strem Chemicals), 4-methoxybenzylamine (329 mg, Tokyo Kasei Kogyo) and sodium tert-butoxide (269 mg, Tokyo Kasei Kogyo) in toluene (5 ml) was stirred with heating at 80° C. under nitrogen atmosphere for 2 hours. The reaction mixture was cooled to room temperature and added with ethyl acetate (5 ml). The insoluble matters were removed by filtration through Celite. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to obtain the title compound (525 mg).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe insoluble matters were removed by filtration through Celite
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

出典と根拠

ORDレコード
ord-2e01521f8a6a49748b5268aa0846e201
出典データセット
uspto-grants-2006_08
特許番号
US07094789B2

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