Dimethylamine, hydrochloride → HCID 178469830, compound

HRID 1373032Notes

Reaction equation

HRID 1373032 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([O:15][C:16]2[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][N:19]=[C:18](SC)[N:17]=2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.O1CCOCC1.ClC1C=CC=C(C(OO)=O)C=1.Cl.[CH3:48][NH:49][CH3:50].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([O:15][C:16]2[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][N:19]=[C:18]([N:49]([CH3:50])[CH3:48])[N:17]=2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 5

HCID 10473Dimethylamine, hydrochlorideHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 204431481,4-Dioxane hydrochlorideHCID 178469864HCID 178469864, compound

Product 1

HCID 178469830HCID 178469830, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

In 50 mL of chloroform was dissolved 2.75 g of N-tert-butoxycarbonyl-trans-4-(5-ethoxycarbonyl-2-methylthiopyrimidin-4-yloxy)cyclohexylamine (a compound of Reference Example 9-49 prior to deprotection (hydrochloric acid-dioxane treatment)), 1.73 g of 75%-m-chloroperbenzoic acid was added to the solution, and the mixture was stirred at room temperature for 30 minutes. Then, 1.14 g of dimethylamine hydrochloride and 2.79 mL of triethylamine were added thereto and the mixture was further stirred for 5 hours. An aqueous saturated sodium hydrogencarbonate solution was added to the reaction mixture, and the mixture was stirred. Then, the chloroform layer was collected by separation, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by silica gel flash chromatography (solvent: hexane-chloroform (50:50 to 100:0)) to obtain 2.74 g of N-tert-butoxycarbonyl-trans-4-[5-ethoxycarbonyl-2-(dimethylamino)-pyrimidin- 4-yloxy]cyclohexylamine.

Workup

  1. stirringthe mixture was further stirred for 5 hours
  2. stirringthe mixture was stirred
  3. customThen, the chloroform layer was collected by separation
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by silica gel flash chromatography (solvent: hexane-chloroform (50:50 to 100:0))

Sources & evidence

ORD record
ord-451b05c4fd924d72a32b135cf0e0b547
Source dataset
uspto-grants-2007_01
Patent number
US07160877B2

Reaction notes

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