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

HRID 2364767Notes

Reaction equation

HRID 2364767 reaction equation
Cl[C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH3:12])[C:7](=[O:13])[C@H:6]([CH2:14][CH3:15])[N:5]([CH:16]([CH3:18])[CH3:17])[C:4]=2[N:3]=1.C[CH:20]1[CH2:24][C:23]2=[C:25]([C:30]([OH:32])=[O:31])[CH:26]=[CH:27][C:28]([NH2:29])=[C:22]2[O:21]1.Cl>C(O)C.O>[CH:16]([N:5]1[C:4]2[N:3]=[C:2]([NH:29][C:28]3[CH:27]=[CH:26][C:25]([C:30]([OH:32])=[O:31])=[C:23]4[C:22]=3[O:21][CH2:20][CH2:24]4)[N:11]=[CH:10][C:9]=2[N:8]([CH3:12])[C:7](=[O:13])[C@@H:6]1[CH2:14][CH3:15])([CH3:18])[CH3:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 68107480Methyl 7-amino-2,3-dihydrobenzofuran-4-carboxylic acidHCID 86668262(7S)-2-chloro-8-isopropyl-7-ethyl-5-methyl-7H-pteridin-6-one

Product 1

HCID 510369997-[[(7S)-8-isopropyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,3-dihydrobenzofuran-4-carboxylic acidYield 57.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

(7S)-2-Chloro-8-isopropyl-7-ethyl-5-methyl-7H-pteridin-6-one 43d (2.50 g, 9.24 mmol) and methyl 7-amino-2,3-dihydrobenzofuran-4-carboxylateic acid 1g (1.50 g, 8.40 mmol) were dissolved in 120 mL of the mixture solvent of ethanol and water (V/V=1:2) followed by the addition of 1.5 mL of concentrated hydrochloric acid. The reaction mixture was heated to reflux for 24 hours with stirring and the precipitate was filtered. The filter cake was washed with dichloromethane (50 mL×3) and dried by heating to obtain the crude compound 7-[[(7S)-8-isopropyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,3-dihydrobenzofuran-4-carboxylic acid 43e (2 g) as a gray solid, which was used in the next step without further furification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 24 hours
  3. filtrationthe precipitate was filtered
  4. washThe filter cake was washed with dichloromethane (50 mL×3)
  5. customdried
  6. temperatureby heating

Sources & evidence

ORD record
ord-1d217de8ecda4d32a1e377ceafecded6
Source dataset
uspto-grants-2014_04
Patent number
US08691822B2

Reaction notes

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