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3-Azabicyclo[3.1.0]hexane hydrochloride → 2-(3-azabicyclo[3.1.0]hexan-3-yl)-4-((3-chloro-4-methoxybenzyl)amino)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-formamide

HRID 2200865
ノート
印刷プレビュー

反応式

HRID 2200865 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[CH2:5][NH:6][C:7]1[C:12]([C:13]([NH:15][CH2:16][C:17]2[N:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[O:14])=[CH:11][N:10]=[C:9](S(C)=O)[N:8]=1.Cl.[CH:32]12[CH2:37][CH:36]1[CH2:35][NH:34][CH2:33]2>C1COCC1.C(N(CC)CC)C>[CH:32]12[CH2:37][CH:36]1[CH2:35][N:34]([C:9]1[N:8]=[C:7]([NH:6][CH2:5][C:4]3[CH:26]=[CH:27][C:28]([O:29][CH3:30])=[C:2]([Cl:1])[CH:3]=3)[C:12]([C:13]([NH:15][CH2:16][C:17]3[N:22]=[CH:21][CH:20]=[CH:19][N:18]=3)=[O:14])=[CH:11][N:10]=1)[CH2:33]2
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 223352893-Azabicyclo[3.1.0]hexane hydrochlorideHCID 86342163Avanafil Impurity K

生成物 1

HCID 732144712-(3-azabicyclo[3.1.0]hexan-3-yl)-4-((3-chloro-4-methoxybenzyl)amino)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-formamide収率 39%

試薬・触媒・溶媒 2

HCID 8471Triethylamine触媒HCID 8028Tetrahydrofuran溶媒

実験手順

In absolute anhydrous THF (10 mL) was dissolved 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylsulphinyl)-N-(pyrimidin-2-ylmethyl) pyrimidine-5-formamide (100 mg, 0.22 mmol). Several drops of triethylamine were added, then 3-azabicyclo[3.1.0]hexan hydrochloride salt (42 mg, 0.35 mmol) was added. The reaction mixture was heated to reflux overnight. The solvent was removed by rotary evaporation, and water was added, followed by extraction with DCM. The organic phase was dried over sodium sulfate and purified by silica gel column chromatography (DCM/methanol=20/1 to 10/1). 2-(3-azabicyclo[3.1.0]hexan-3-yl)-4-((3-chloro-4-methoxybenzyl)amino)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-formamide as a white solid was obtained (40 mg, 39% yield).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight
  3. customThe solvent was removed by rotary evaporation, and water
  4. additionwas added
  5. extractionfollowed by extraction with DCM
  6. dry with materialThe organic phase was dried over sodium sulfate
  7. custompurified by silica gel column chromatography (DCM/methanol=20/1 to 10/1)

出典と根拠

ORDレコード
ord-1131e03a8a7a4daa893f65f732202ed1
出典データセット
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09359371B2

反応ノート

読み込み中…

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