Ammonia → HCID 178424855、化合物

HRID 49220ノート

反応式

HRID 49220 の反応式
[CH:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([NH2:10])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].Cl[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH2:22][CH2:23][C:24]2[CH:25]=[N:26][C:27]([CH3:30])=[CH:28][CH:29]=2)=[CH:14][N:13]=1.N.O>CCOC(C)=O>[CH:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([NH:10][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([CH2:22][CH2:23][C:24]3[CH:25]=[N:26][C:27]([CH3:30])=[CH:28][CH:29]=3)=[CH:14][N:13]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 222AmmoniaHCID 962WaterHCID 17948435HCID 17948435、化合物HCID 178448118HCID 178448118、化合物

生成物 1

HCID 178424855HCID 178424855、化合物

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

Under a N2 atmosphere, 600 mg (4.25 mmol) of trans-4-isopropyl-cyclo-hexylamine [for preparation see Arzneim. Forsch. 19 (1969), 140] and 120 mg (0.424 mmol) of 1-chloro-4-[2-(6-methyl-pyridin-3-yl)-ethyl]-isoquinoline are heated to 140° C. in an ampulla for 10 h. The reaction mixture is suspended in EtOAc, and mixed with 0.25 ml of NH3 solution (25%) and water. The separated aqueous phase is extracted twice more with EtOAc, the organic phases washed with water and brine, dried (Na2SO4) and concentrated by evaporation. Column chromatography (SiO2; hexane/EtOAc 1:1) yields trans 1-(4-isopropyl-cyclohexylamino)-4-[2-(6-methyl-pyridin-3-yl)-ethyl]-isoquinoline; 1H NMR (DMSO-d6) δ8.27 (m, 2H), 7.88 (d, 1H), 7.65 (t, 1H), 7.60 (s, 1H), 7.54 (m, 1H), 7.45 (t, 1H), 7.14 (d, 1H), 6.84 (d, 1H), 3.88 (m, 1H), 3.00 (m, 2H), 2.84 (m, 2H), 2.40 (s, 3H), 2.00 (m, 2H), 1.71 (m, 2H), 1.5-1.0 (m, 6H), 0.86 (d, 6H).

後処理

  1. extractionThe separated aqueous phase is extracted twice more with EtOAc
  2. washthe organic phases washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated by evaporation

出典と根拠

ORDレコード
ord-defd66c4dbba4204bd9a0225e3241536
出典データセット
uspto-grants-2004_03
特許番号
US06706731B2

反応ノート

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