2-(Methylamino)ethanol → HCID 67198110, compound

HRID 550805Notes

Reaction equation

HRID 550805 reaction equation
[C:1](=[O:39])(OC1C=CC([N+]([O-])=O)=CC=1)[O:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[C:10]3[CH2:26][S:25](=[O:28])(=[O:27])[CH2:24][C:11]=3[N:12]=[C:13]([C:15]3[CH:20]=[C:19]([F:21])[C:18]([Cl:22])=[CH:17][C:16]=3[F:23])[N:14]=2)[CH2:5][CH2:4]1.[CH3:40][NH:41][CH2:42][CH2:43][OH:44].C(=O)(O)[O-].[Na+].Cl.O1CCOCC1>C1COCC1.CN(C=O)C>[ClH:22].[OH:44][CH2:43][CH2:42][N:41]([CH3:40])[C:1](=[O:39])[O:2][CH:3]1[CH2:4][CH2:5][N:6]([C:9]2[C:10]3[CH2:26][S:25](=[O:27])(=[O:28])[CH2:24][C:11]=3[N:12]=[C:13]([C:15]3[CH:20]=[C:19]([F:21])[C:18]([Cl:22])=[CH:17][C:16]=3[F:23])[N:14]=2)[CH2:7][CH2:8]1

Participants

7

Reactant 4

HCID 80162-(Methylamino)ethanolHCID 516892Sodium BicarbonateHCID 204431481,4-Dioxane hydrochlorideHCID 67195545HCID 67195545, compound

Product 1

HCID 67198110HCID 67198110, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 300 mg of 1-[2-(4-chloro-2,5-difluorophenyl)-6,6-dioxido-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperidin-4-yl 4-nitrophenyl carbonate, 43 mg of 2-(methylamino)ethanol, and 5 ml of DMF was stirred at ambient temperature for 19.5 hours. Saturated aqueous sodium bicarbonate solution was added to the reaction mixture, the mixture was extracted twice with chloroform. The organic phase was washed with brine, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The yellow oil obtained was dissolved in THF, here was added 4M HCl-dioxane solution, and the solution was concentrated under reduced pressure to give solid, which was recrystallized from acetonitrile-ether to yield 120 mg of 1-[2-(4-chloro-2,5-difluorophenyl)-6,6-dioxido-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperidin-4-yl (2-hydroxyethyl)methylcarbamate hydrochloride as colorless solid.

Workup

  1. extractionthe mixture was extracted twice with chloroform
  2. washThe organic phase was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe yellow oil obtained
  6. concentrationthe solution was concentrated under reduced pressure
  7. customto give solid, which
  8. customwas recrystallized from acetonitrile-ether

Sources & evidence

ORD record
ord-5bc0532bb9ff4d749501da4aea35dac8
Source dataset
uspto-grants-2011_05
Patent number
US07947690B2

Reaction notes

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