Triethylamine → HCID 136380438, compound

HRID 489423Notes

Reaction equation

HRID 489423 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]#[N:15])=[C:12]([CH2:16][CH2:17][CH3:18])[NH:11][C:10]2=[N:19][NH:20][C:21]([OH:22])=[C:9]12.C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[C:39]([O:43][C:44](=O)[O:45]C(C)(C)C)([CH3:42])([CH3:41])[CH3:40]>C1COCC1>[C:39]([O:43][C:44]([O:22][C:21]1[C:9]2[CH:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[C:13]([C:14]#[N:15])=[C:12]([CH2:16][CH2:17][CH3:18])[NH:11][C:10]=2[NH:19][N:20]=1)=[O:45])([CH3:42])([CH3:41])[CH3:40]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 178439375HCID 178439375, compound

Product 1

HCID 136380438HCID 136380438, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2-chlorophenyl)-5-cyano-4,7-dihydro-3-hydroxy-6-propyl-2H-pyrazolo[3,4-b]pyridine (12.5 g) in THF (400 mL) was added triethylamine (4.5 g), dimethylaminopyridine (0.5 g) and di-t-butylcarbonate (9.6 g) and the mixture was stirred for 3 hours. The mixture was extracted with ethyl acetate and the solvent was evaporated under reduced pressure. The residue was recrystallized from ethyl acetate to give the title compound (12 g) as colorless crystals.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-1ec94aaeb84f4e4092c35c327fcc2213
Source dataset
uspto-grants-2005_12
Patent number
US06977262B2

Reaction notes

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