Tetrahydrofuran → HCID 58662445, compound

HRID 644807Notes

Reaction equation

HRID 644807 reaction equation
[CH2:1]([O:8][C:9](=[O:24])[NH:10][CH:11]1[CH2:16][CH:15]([CH2:17][CH3:18])[NH:14][C:13]2[N:19]([CH3:23])[N:20]=[C:21]([CH3:22])[C:12]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.C(=O)([O-])[O-].[K+].[K+].Cl[C:37]([O:39][CH2:40][CH3:41])=[O:38]>O>[CH2:40]([O:39][C:37]([N:14]1[CH:15]([CH2:17][CH3:18])[CH2:16][CH:11]([NH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:24])[C:12]2[C:21]([CH3:22])=[N:20][N:19]([CH3:23])[C:13]1=2)=[O:38])[CH3:41]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 136002823HCID 136002823, compound

Product 1

HCID 58662445HCID 58662445, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(6-Ethyl-1,3-dimethyl-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-b]pyridine-4-yl)-carbamic acid benzyl ester (0.35 g, 1.08 mmol) obtained in step (ii), dry THF (5 mL) and potassium carbonate (0.45 g, 3.2 mmol) were charged to a flask under a nitrogen atomsphere. This mixture was stirred at room temperature for about 0.5 h, after which time ethyl chloroformate (0.47 g, 3.2 mmol) was added drop-wise. This reaction mixture was then stirred for about 4 h, water was added to the mixture, and the aqueous layer was extracted with ethyl acetate (3×10 mL). The combined organic layer was washed with brine (1×20 mL), dried over sodium sulphate, and concentrated under vacuum to afford the title compound (0.375 g, 88%).

Workup

  1. stirringThis reaction mixture was then stirred for about 4 h
  2. extractionthe aqueous layer was extracted with ethyl acetate (3×10 mL)
  3. washThe combined organic layer was washed with brine (1×20 mL)
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-00025a295d5a459f8cc0feb5166e5580
Source dataset
uspto-grants-2010_04
Patent number
US07700774B2

Reaction notes

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