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1-Methyl-3-pyrrolidinol → 2-({[2-(4-Chlorophenyl)-1,3-thiazol-4-yl]methyl}sulphanyl)-6-[(1-methylpyrrolidin-3-yl)oxy]-4-phenylpyridine-3,5-dicarbonitrile

HRID 1500114
ノート
印刷プレビュー

反応式

HRID 1500114 の反応式
[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([CH3:7])[CH2:3]1.Cl[C:9]1[C:14]([C:15]#[N:16])=[C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([C:23]#[N:24])=[C:11]([S:25][CH2:26][C:27]2[N:28]=[C:29]([C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=3)[S:30][CH:31]=2)[N:10]=1>C1COCC1>[Cl:38][C:35]1[CH:36]=[CH:37][C:32]([C:29]2[S:30][CH:31]=[C:27]([CH2:26][S:25][C:11]3[C:12]([C:23]#[N:24])=[C:13]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:14]([C:15]#[N:16])=[C:9]([O:1][CH:2]4[CH2:6][CH2:5][N:4]([CH3:7])[CH2:3]4)[N:10]=3)[N:28]=2)=[CH:33][CH:34]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 930741-Methyl-3-pyrrolidinolHCID 866542112-Chloro-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}sulphanyl)-4-phenylpyridine-3,5-dicarbonitrile

生成物 1

HCID 445487102-({[2-(4-Chlorophenyl)-1,3-thiazol-4-yl]methyl}sulphanyl)-6-[(1-methylpyrrolidin-3-yl)oxy]-4-phenylpyridine-3,5-dicarbonitrile

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

25 μl (0.229 mmol) of 3-hydroxy-N-methylpyrrolidine are initially charged in 0.5 ml of THF, the mixture is cooled to 0° C., 249 μl (0.249 mmol) of phosphazene base P(4)-t-Bu (1M in THF) are added and the mixture is stirred at this temperature for 10 minutes. 120 mg (0.208 mmol) of the compound from Example 3A are then added, and the mixture is stirred at RT overnight. The reaction mixture is then purified by preparative HPLC (addition of 0.15% hydrochloric acid). This gives 38 mg of the impure target compound. This is dissolved in dichloromethane and washed twice with 1N hydrochloric acid, once with water and once with saturated aqueous sodium chloride solution. After drying over sodium sulphate, the organic phase is concentrated on a rotary evaporator and the crude product is purified once more by preparative HPLC (addition of 0.15% hydrochloric acid).

後処理

  1. stirringthe mixture is stirred at RT overnight
  2. customThe reaction mixture is then purified by preparative HPLC (addition of 0.15% hydrochloric acid)
  3. dissolutionThis is dissolved in dichloromethane
  4. washwashed twice with 1N hydrochloric acid, once with water and once with saturated aqueous sodium chloride solution
  5. dry with materialAfter drying over sodium sulphate
  6. concentrationthe organic phase is concentrated on a rotary evaporator
  7. customthe crude product is purified once more by preparative HPLC (addition of 0.15% hydrochloric acid)

出典と根拠

ORDレコード
ord-f80126a3d1c64baf97d3b1c4677e0f09
出典データセット
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09205077B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート