Triethylamine → tert-butyl 2-{[4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl]methyl}-2,7-diazaspiro[3.5]nonane-7-carboxylate

HRID 1253527Notes

Reaction equation

HRID 1253527 reaction equation
[CH3:1][O:2][C:3]1[C:4]2[N:5]([N:15]=[CH:16][C:17]=2[CH:18]=O)[CH:6]=[C:7]([C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)[CH:8]=1.[Cl-].[C:21]([O:25][C:26]([N:28]1[CH2:36][CH2:35][C:31]2([CH2:34][NH2+:33][CH2:32]2)[CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:23])[CH3:22].C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:1][O:2][C:3]1[C:4]2[N:5]([N:15]=[CH:16][C:17]=2[CH2:18][N:33]2[CH2:34][C:31]3([CH2:30][CH2:29][N:28]([C:26]([O:25][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:27])[CH2:36][CH2:35]3)[CH2:32]2)[CH:6]=[C:7]([C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)[CH:8]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 866570544-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine-3-carbaldehydeHCID 178451559HCID 178451559, compound

Product 1

HCID 67207321tert-butyl 2-{[4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl]methyl}-2,7-diazaspiro[3.5]nonane-7-carboxylate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine-3-carbaldehyde (25.0 mg, 0.098 mmol), 7-(tert-butoxycarbonyl)-7-aza-2-azoniaspiro[3.5]nonane chloride (39.0 mg, 0.15 mmol), and triethylamine (0.054 mL, 0.39 mmol) in 1,2-dichloroethane (2 ml) was added sodium triacetoxyborohydride (41.0 mg, 0.20 mmol). After 2 h, the reaction was quenched with saturated aqueous sodium hydrogen carbonate, diluted with ethyl acetate, dried over magnesium sulfate, filtered and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate/isohexane gradient) to give tert-butyl 2-{[4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl]methyl}-2,7-diazaspiro[3.5]nonane-7-carboxylate. LRMS (ESI) calculated for C25H35N6O3 [M+H]+, 467.3; found 467.1.

Workup

  1. customthe reaction was quenched with saturated aqueous sodium hydrogen carbonate
  2. additiondiluted with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (ethyl acetate/isohexane gradient)

Sources & evidence

ORD record
ord-e7f9e4cfe51343ca83aad14d2d76f090
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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