Sodium Hydroxide → N-(1H-benzoimidazol-2-ylmethyl)-N'-pyrimidin-2-ylmethyl-N-(5,6,7,8-tetrahydro-quinolin-8-yl)-butane-1,4-diamine

HRID 899746ノート

反応式

HRID 899746 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[CH:7]=O.[NH:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[CH2:18][N:19]([CH:25]1[C:34]2[N:33]=[CH:32][CH:31]=[CH:30][C:29]=2[CH2:28][CH2:27][CH2:26]1)[CH2:20][CH2:21][CH2:22][CH2:23][NH2:24].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>C1COCC1.Br.CC(O)=O>[NH:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[CH2:18][N:19]([CH:25]1[C:34]2[N:33]=[CH:32][CH:31]=[CH:30][C:29]=2[CH2:28][CH2:27][CH2:26]1)[CH2:20][CH2:21][CH2:22][CH2:23][NH:24][CH2:7][C:2]1[N:3]=[CH:4][CH:5]=[CH:6][N:1]=1

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 10126019N'-(1H-benzimidazol-2-ylmethyl)-N'-(5,6,7,8-tetrahydroquinolin-8-yl)butane-1,4-diamineHCID 13751953Pyrimidine-2-carbaldehyde

生成物 1

HCID 10127385N-(1H-benzoimidazol-2-ylmethyl)-N'-pyrimidin-2-ylmethyl-N-(5,6,7,8-tetrahydro-quinolin-8-yl)-butane-1,4-diamine

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 21893785Acetic Acid Mixture with Hydrobromic Acid溶媒

実験手順

Using General Procedure B: To a solution of the crude aldehyde from above (332 mg) and N′-(1H-benzoimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-quinolin-8-yl)-butane-1,4-diamine (49 mg, 0.14 mmol) in THF (2 mL) was added NaBH(OAc)3 (89 mg, 0.42 mmol) and the mixture was stirred at room temperature for 1.5 h. The crude material was dissolved in saturated HBr/AcOH (2 mL) and stirred at room temperature for 5 minutes. The solution was made basic with 10 N NaOH(aq) and extracted with CH2Cl2 (3×15 mL). The combined organic extracts were dried (MgSO4) and concentrated in vacuo. Purification of the crude material by column chromatography on silica gel (200:5:1 CH2Cl2/MeOH/NH4OH) afforded a yellow oil (44 mg).

後処理

  1. stirringstirred at room temperature for 5 minutes
  2. extractionextracted with CH2Cl2 (3×15 mL)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customPurification of the crude material by column chromatography on silica gel (200:5:1 CH2Cl2/MeOH/NH4OH)

出典と根拠

ORDレコード
ord-b686d0e23c39411481fbdafea9f52a46
出典データセット
uspto-grants-2008_04
特許番号
US07354934B2

反応ノート

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