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 899746노트

반응식

HRID 899746 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 21893785Acetic Acid Mixture with Hydrobromic Acid용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-b686d0e23c39411481fbdafea9f52a46
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07354934B2

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