Hydrochloric Acid → 7-[(8-Cyclopentyl-7,7-diethyl-5-methyl-6-oxo-pteridin-2-yl)amino]-2,3-dihydrobenzofuran-4-carboxylic acid

HRID 2364761Notes

Reaction equation

HRID 2364761 reaction equation
Cl[C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH3:12])[C:7](=[O:13])[C:6]([CH2:16][CH3:17])([CH2:14][CH3:15])[N:5]([CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[C:4]=2[N:3]=1.C[CH:24]1[CH2:28][C:27]2=[C:29]([C:34]([OH:36])=[O:35])[CH:30]=[CH:31][C:32]([NH2:33])=[C:26]2[O:25]1.Cl>C(O)C.O>[CH:18]1([N:5]2[C:4]3[N:3]=[C:2]([NH:33][C:32]4[CH:31]=[CH:30][C:29]([C:34]([OH:36])=[O:35])=[C:27]5[C:26]=4[O:25][CH2:24][CH2:28]5)[N:11]=[CH:10][C:9]=3[N:8]([CH3:12])[C:7](=[O:13])[C:6]2([CH2:16][CH3:17])[CH2:14][CH3:15])[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 68107480Methyl 7-amino-2,3-dihydrobenzofuran-4-carboxylic acidHCID 866682582-Chloro-8-cyclopentyl-7,7-diethyl-5-methyl-pteridin-6-one

Product 1

HCID 681073747-[(8-Cyclopentyl-7,7-diethyl-5-methyl-6-oxo-pteridin-2-yl)amino]-2,3-dihydrobenzofuran-4-carboxylic acidYield 38.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2-Chloro-8-cyclopentyl-7,7-diethyl-5-methyl-pteridin-6-one 42a (100 mg, 0.31 mmol) and methyl 7-amino-2,3-dihydrobenzofuran-4-carboxylic acid 1g (50 mg, 0.28 mmol) were dissolved in 17 mL of the mixture solvent of ethanol and water (V/V=5:12) followed by the addition of 0.2 mL of concentrated hydrochloric acid. The reaction mixture was heated to reflux for 16 hours with stirring. The resulting solution was concentrated under reduced pressure, added dropwise with 1 M lithium hydroxide solution to adjust pH to 12 and extracted with ethyl acetate (50 mL×2), the combined aqueous phase was added dropwise with 1 M hydrochloric acid to adjust pH to 1 and extracted with dichloromethane (50 mL×3). The combined organic phase was dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure to obtain 7-[(8-cyclopentyl-7,7-diethyl-5-methyl-6-oxo-pteridin-2-yl)amino]-2,3-dihydrobenzofuran-4-carboxylic acid 42b (50 mg, yield: 38.0%) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 16 hours
  3. concentrationThe resulting solution was concentrated under reduced pressure
  4. additionadded dropwise with 1 M lithium hydroxide solution
  5. extractionextracted with ethyl acetate (50 mL×2)
  6. additionthe combined aqueous phase was added dropwise with 1 M hydrochloric acid
  7. extractionextracted with dichloromethane (50 mL×3)
  8. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b0ddba457c6e446088fc14a19a9bea45
Source dataset
uspto-grants-2014_04
Patent number
US08691822B2

Reaction notes

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