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 2253389Notes

Reaction equation

HRID 2253389 reaction equation
[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

Participants

8

Reactant 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

Product 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-pyranylmethylamineYield 63.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b16df8c3dd4843ee9b60abdff1b362f9
Source dataset
uspto-grants-2008_01
Patent number
US07323569B2

Reaction notes

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