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Sodium Bicarbonate → N-Cyclopropylmethyl-N-[7-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-2-(methoxymethyl)pyrazolo[1,5-a]pyridin-3-yl]-N-tetrahydro-2H-4-pyranylmethylamine

HRID 347855
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HRID 347855 반응식
[CH:1]1([CH2:4][NH:5][C:6]2[C:7]([CH2:28][O:29][CH3:30])=[N:8][N:9]3[C:14]([C:15]4[C:20]([O:21][CH3:22])=[CH:19][C:18]([CH2:23][O:24][CH3:25])=[CH:17][C:16]=4[O:26][CH3:27])=[CH:13][CH:12]=[CH:11][C:10]=23)[CH2:3][CH2:2]1.[O:31]1[CH2:36][CH2:35][CH:34]([CH:37]=O)[CH2:33][CH2:32]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1.C(OCC)(=O)C.O>[CH:1]1([CH2:4][N:5]([C:6]2[C:7]([CH2:28][O:29][CH3:30])=[N:8][N:9]3[C:14]([C:15]4[C:16]([O:26][CH3:27])=[CH:17][C:18]([CH2:23][O:24][CH3:25])=[CH:19][C:20]=4[O:21][CH3:22])=[CH:13][CH:12]=[CH:11][C:10]=23)[CH2:37][CH:34]2[CH2:35][CH2:36][O:31][CH2:32][CH2:33]2)[CH2:3][CH2:2]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 9964078Tetrahydro-2H-pyran-4-carboxaldehydeHCID 21084165N-Cyclopropylmethyl-N-[7-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-2-(methoxymethyl)pyrazolo[1,5-a]pyridin-3-yl]amine

생성물 1

HCID 58801633N-Cyclopropylmethyl-N-[7-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-2-(methoxymethyl)pyrazolo[1,5-a]pyridin-3-yl]-N-tetrahydro-2H-4-pyranylmethylamine
수율 63.6%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of N-cyclopropylmethyl-N-[7-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-2-(methoxymethyl)pyrazolo[1,5-a]pyridin-3-yl]amine (80 mg) dissolved in tetrahydrofuran (2 mL) was added tetrahydropyran-4-carbaldehyde (44 mg) and sodium triacetoxyborohydride (82 mg), and the reaction mixture was stirred for 30 minutes at room temperature. Water and saturated aqueous sodium bicarbonate were added to the reaction mixture, extraction was performed with ethyl acetate and the organic extract was washed with brine. The organic extract was dried over anhydrous magnesium sulfate and filtered, the solvent was evaporated under reduced pressure, the residue was purified by silica gel column chromatography and the title compound (63 mg) was obtained as a yellow oil from the n-hexane:ethyl acetate (1:2) fraction.

후처리

  1. extractionthe organic extract
  2. washwas washed with brine
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-0b4cbb92390f48369c8159a1b49337cb
출처 데이터셋
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07176216B2

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