Sulfuric Acid → N-Cyclopropylmethyl-N-[7-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-2-(methoxymethyl)pyrazolo[1,5-a]pyridin-3-yl]-N-tetrahydro-3-furanylmethylamine

HRID 2253390Notes

Reaction equation

HRID 2253390 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[CH2:35][CH2:34][CH:33]([CH:36]=O)[CH2:32]1.S(=O)(=O)(O)O.[BH4-].[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)[CH2:36][CH:33]2[CH2:34][CH2:35][O:31][CH2:32]2)[CH2:3][CH2:2]1

Participants

9

Reactant 5

HCID 1118Sulfuric AcidHCID 1575683-Furancarboxaldehyde, tetrahydro-HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 21084165N-Cyclopropylmethyl-N-[7-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-2-(methoxymethyl)pyrazolo[1,5-a]pyridin-3-yl]amine

Product 1

HCID 21084167N-Cyclopropylmethyl-N-[7-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-2-(methoxymethyl)pyrazolo[1,5-a]pyridin-3-yl]-N-tetrahydro-3-furanylmethylamine

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 (15 mg) dissolved in tetrahydrofuran (1 mL) was added tetrahydrofuran-3-carbaldehyde (50% aqueous solution; 0.022 mL), a 3M aqueous sulfuric acid solution (0.036 mL) and sodium borohydride (2.8 mg) while cooling with ice and the reaction mixture was stirred for 1 hour at the same temperature. Water and then saturated aqueous sodium bicarbonate were added to the obtained reaction mixture, extraction was performed with ethyl acetate, the organic extract was washed with brine, dried over anhydrous magnesium sulfate and filtered, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography and the title compound (4.8 mg) was obtained as light yellow crystals from the n-hexane:ethyl acetate (1:2) fraction.

Workup

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

Sources & evidence

ORD record
ord-33051a8dd2994344b2c23c7ee3f13ec3
Source dataset
uspto-grants-2008_01
Patent number
US07323569B2

Reaction notes

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