Sodium Bicarbonate → N-(tert-butoxycarbonyl)-N'-(4-chloro-5-isoquinolyl)-1,4-cyclohexanediamine

HRID 10553

반응식

HRID 10553 반응식
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH2:12])[CH:5]=[N:4][CH:3]=1.O=[C:14]1[CH2:19][CH2:18][C:17](C(OC(C)(C)C)=O)([NH2:20])[CH2:16][CH2:15]1.[BH4-].[Na+].[C:30](=[O:33])([O-])[OH:31].[Na+]>CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4].CO.ClCCl>[C:6]([O:31][C:30]([NH:20][CH:17]1[CH2:16][CH2:15][CH:14]([NH:12][C:10]2[CH:9]=[CH:8][CH:7]=[C:6]3[C:11]=2[C:2]([Cl:1])=[CH:3][N:4]=[CH:5]3)[CH2:19][CH2:18]1)=[O:33])([CH3:11])([CH3:7])[CH3:5]

참가 물질

8

반응물 4

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 219799374-Chloroisoquinolin-5-amineHCID 21979990Tert-butyl 4-oxo-1-aminocyclohexylcarboxylate

생성물 1

HCID 21979991N-(tert-butoxycarbonyl)-N'-(4-chloro-5-isoquinolyl)-1,4-cyclohexanediamine

시약·촉매·용매 3

HCID 11026Titanium isopropoxide촉매HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

According to the method of Example 103, Step A, a mixture of Intermediate 90 (100 mg), tert-butyl 4-oxo-1-aminocyclohexylcarboxylate (270 mg), titanium tetraisopropoxide (0.34 ml) and dichloromethane (7 ml) was stirred at room temperature for 120 hours. The reaction mixture was added with sodium borohydride (94 mg) and methanol (1 ml) and stirred for 1.5 hours with ice cooling. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate (10 ml) with ice cooling and then extracted twice with ethyl acetate (15 ml for each time). The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to obtain the title compound (40.4 mg).

후처리

  1. stirringstirred for 1.5 hours with ice cooling
  2. extractionextracted twice with ethyl acetate (15 ml for each time)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

출처 및 근거

ORD 기록
ord-2183330ad69d4daf8b0bf3debc9cee84
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094789B2

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