Tetrahydrofuran → HCID 66645490, compound

HRID 44677Notes

Reaction equation

HRID 44677 reaction equation
C([N:20]1[C:24]2[N:25]=[CH:26][CH:27]=[C:28]([C:29](=[S:31])[NH2:30])[C:23]=2[CH:22]=[N:21]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.Br[CH:33]1[CH2:38][CH2:37][CH2:36][C:35]([CH3:41])([C:39]#[N:40])[C:34]1=O.C1COCC1>CCO>[CH3:41][C:35]1([C:39]#[N:40])[C:34]2[N:30]=[C:29]([C:28]3[CH:27]=[CH:26][N:25]=[C:24]4[NH:20][N:21]=[CH:22][C:23]=34)[S:31][C:33]=2[CH2:38][CH2:37][CH2:36]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 68088970HCID 68088970, compoundHCID 866678811-trityl-1H-pyrazolo[3,4-b]pyridine-4-carbothioamide

Product 1

HCID 66645490HCID 66645490, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-tritylpyrazolo[5,4-b]pyridine-4-carbothioamide (220 mg, 0.5232 mmol) and 3-bromo-1-methyl-2-oxo-cyclohexane-1-carbonitrile (125.0 mg, 0.5785 mmol) in EtOH (10 mL)/THF (1.5 mL) was heated at 90° C. overnight under nitrogen. The reaction mixture was concentrated in vacuo and purified by column chromatography (70:9:1 DCM/MeOH/NH4OH) to give a white solid after precipitation (67 mg, 39% Yield). MS (ES+) 296.08

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by column chromatography (70:9:1 DCM/MeOH/NH4OH)
  3. customto give a white solid
  4. customafter precipitation (67 mg, 39% Yield)

Sources & evidence

ORD record
ord-ba4521b8bf1b4d45a71aa0f8ccaca72f
Source dataset
uspto-grants-2013_09
Patent number
US08541445B2

Reaction notes

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