Hydrochloric Acid → HCID 68107050, compound

HRID 2364752Notes

Reaction equation

HRID 2364752 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:14]([OH:16])=[O:15])=[C:6]2[C:10]=1[O:9][CH:8]([CH2:11][O:12][CH3:13])[CH2:7]2.Cl[C:18]1[N:27]=[CH:26][C:25]2[N:24]([CH3:28])[C:23](=[O:29])[C@@H:22]([CH2:30][CH3:31])[N:21]([CH:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)[C:20]=2[N:19]=1.Cl>C(O)C.O>[CH:32]1([N:21]2[C:20]3[N:19]=[C:18]([NH:1][C:2]4[CH:3]=[CH:4][C:5]([C:14]([OH:16])=[O:15])=[C:6]5[C:10]=4[O:9][CH:8]([CH2:11][O:12][CH3:13])[CH2:7]5)[N:27]=[CH:26][C:25]=3[N:24]([CH3:28])[C:23](=[O:29])[C@H:22]2[CH2:30][CH3:31])[CH2:33][CH2:34][CH2:35][CH2:36]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24820413(R)-2-Chloro-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-oneHCID 68106972HCID 68106972, compound

Product 1

HCID 68107050HCID 68107050, compoundYield 44.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

7-Amino-2-(methoxymethyl)-2,3-dihydrobenzofuran-4-carboxylic acid 40d (160 mg, 0.70 mmol) and (7R)-2-chloro-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydro-5H-pteridin-6-one 1o (232 mg, 0.80 mmol) were dissolved in 34 mL of the mixture solvent of ethanol and water (V:V=1:2.4) followed by the addition of 0.4 mL of concentrated hydrochloric acid. The reaction solution was heated to reflux for 16 hours with stirring, then cooled down resulting in the formation of precipitate. The precipitate was filtered to obtain the title compound 7-[[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2-(methoxymethyl)-2,3-dihydrobenzofuran-4-carboxylic acid 40e (0.15 g, yield: 43.0%) as a yellow solid.

Workup

  1. temperatureThe reaction solution was heated
  2. temperatureto reflux for 16 hours
  3. temperaturecooled down
  4. customresulting in the formation of precipitate
  5. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-bc6f4c64022d4128beb4931f76879b73
Source dataset
uspto-grants-2014_04
Patent number
US08691822B2

Reaction notes

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