Glycolic Acid → HCID 18447083, compound

HRID 1269901Notes

Reaction equation

HRID 1269901 reaction equation
[OH:1][CH2:2][C:3]([OH:5])=O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[CH:28]12[NH:35][CH:32]([CH2:33][CH2:34]1)[CH2:31][CH:30]([NH:36][C:37]1[CH:38]=[C:39]3[C:43](=[CH:44][CH:45]=1)[NH:42][N:41]=[CH:40]3)[CH2:29]2.C(=O)([O-])O.[Na+]>CN(C)C=O>[NH:42]1[C:43]2[C:39](=[CH:38][C:37]([NH:36][CH:30]3[CH2:31][CH:32]4[N:35]([C:3](=[O:5])[CH2:2][OH:1])[CH:28]([CH2:34][CH2:33]4)[CH2:29]3)=[CH:45][CH:44]=2)[CH:40]=[N:41]1

Participants

7

Reactant 5

HCID 757Glycolic AcidHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18447426HCID 18447426, compound

Product 1

HCID 18447083HCID 18447083, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Hydroxyacetic acid (32 mg, 0.421 mmol), 1-hydroxybenzotriazole (76 mg, 0.496 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (95 mg, 0.496 mmol) were added in that order to a suspension of the N-(8-azabicyclo[3.2.1]oct-3-yl)-1H-indazol-5-amine (100 mg, 0.413 mmol) obtained in Example 525 in dimethylformamide (1 ml), and the resulting mixture was stirred at room temperature for 23 hours. The reaction mixture was poured into a saturated aqueous sodium hydrogencarbonate solution to terminate the reaction, and was extracted twice with ethyl acetate. The extract solution was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, and then distilled under reduced pressure to remove the solvent, whereby a crude product was obtained. The crude product was purified by a preparative thin-layer chromatography (200×200×0.5 mm, 4 plates, eluent: chloroform/methanol=15/1) to obtain 2-[3-(1H-indazol-5-ylamino)-8-azabicyclo[3.2.1]oct-8-yl]-2-oxoethanol (13 mg, 11%).

Workup

  1. customto terminate
  2. customthe reaction
  3. extractionwas extracted twice with ethyl acetate
  4. washThe extract solution was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent, whereby a crude product
  8. customwas obtained
  9. customThe crude product was purified by a preparative thin-layer chromatography (200×200×0.5 mm, 4 plates, eluent: chloroform/methanol=15/1)

Sources & evidence

ORD record
ord-ebc592f5782f4856a2fde55646ecb122
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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