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Methyl morpholine oxide → (4RS,5SR)-1-[2-(4-chloro-2,5-difluorophenyl)thieno[3,2-d]pyrimidine-4-yl]azepane-4,5-diol hydrochloride

HRID 225488
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HRID 225488 반응식
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[N:10]=[C:11]([N:18]3CCC=C[CH2:20][CH2:19]3)[C:12]3[S:17][CH:16]=[CH:15][C:13]=3[N:14]=2)=[C:4]([F:25])[CH:3]=1.C[N+]1([O-])CC[O:30]CC1.[CH2:34]1[CH2:38][O:37][CH2:36][CH2:35]1.O.Cl.CCOC(C)=O>C1COCC1.[Os](=O)(=O)(=O)=O.C(O)(C)(C)C.O>[ClH:1].[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[N:10]=[C:11]([N:18]3[CH2:38][CH2:34][CH:35]([OH:30])[CH:36]([OH:37])[CH2:20][CH2:19]3)[C:12]3[S:17][CH:16]=[CH:15][C:13]=3[N:14]=2)=[C:4]([F:25])[CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 82029Methyl morpholine oxideHCID 21866389Hydrogen chloride-ethyl acetateHCID 21881883Oxolane--water (1/1)HCID 690759792-(4-chloro-2,5-difluorophenyl)-4-(2,3,6,7-tetrahydro-1H-azepine-1-yl)thieno[3,2-d]pyrimidine

생성물 1

HCID 69079363(4RS,5SR)-1-[2-(4-chloro-2,5-difluorophenyl)thieno[3,2-d]pyrimidine-4-yl]azepane-4,5-diol hydrochloride

시약·촉매·용매 3

HCID 87401860HCID 87401860, 화합물촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 582 mg of 2-(4-chloro-2,5-difluorophenyl)-4-(2,3,6,7-tetrahydro-1H-azepine-1-yl)thieno[3,2-d]pyrimidine, 235 mg of N-methylmorpholine-N-oxide, 1.30 ml of 2.5 w % osmium tetroxide-tert-butanol solution and 10 ml of THF-water (4:1) was stirred for 20 hours at room temperature. After 50 ml of water was added to the reaction mixture and extracted with EtOAc, the resultant washed with a saturated saline solution. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure. the obtained residue was purified by silica gel column chromatography (chloroform-MeOH) to give a foam-like substance. After the obtained foam-like substance was dissolved in 20 ml of THF and 2 ml of 4M HCl-EtOAc solution was added, it was concentrated under reduced pressure to give a solid. This solid was recrystallized from EtOH-ether to give 618 mg of (4RS,5SR)-1-[2-(4-chloro-2,5-difluorophenyl)thieno[3,2-d]pyrimidine-4-yl]azepane-4,5-diol hydrochloride.

후처리

  1. extractionextracted with EtOAc
  2. washthe resultant washed with a saturated saline solution
  3. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (chloroform-MeOH)
  6. customto give a foam-like substance
  7. concentrationit was concentrated under reduced pressure
  8. customto give a solid
  9. customThis solid was recrystallized from EtOH-ether

출처 및 근거

ORD 기록
ord-2fc93ec8becc49c9ad23730716f1cdf3
출처 데이터셋
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07557112B2

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