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

HRID 10553

反応式

HRID 10553 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 11026Titanium isopropoxide触媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-2183330ad69d4daf8b0bf3debc9cee84
出典データセット
uspto-grants-2006_08
特許番号
US07094789B2

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