Hydrochloric Acid → HCID 68107395, compound

HRID 2364733Notes

Reaction equation

HRID 2364733 reaction equation
[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([NH:16][C:17]4[CH:18]=[CH:19][C:20]([C:27]([O-:29])=[O:28])=[C:21]5[C:25]=4[O:24][CH:23]([CH3:26])[CH2:22]5)[N:12]=[CH:11][C:10]=3[N:9]([CH3:30])[C:8](=[O:31])[C@H:7]2[CH2:32][CH3:33])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Li+].Cl>CO.O1CCCC1>[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([NH:16][C:17]4[CH:18]=[CH:19][C:20]([C:27]([OH:29])=[O:28])=[C:21]5[C:25]=4[O:24][CH:23]([CH3:26])[CH2:22]5)[N:12]=[CH:11][C:10]=3[N:9]([CH3:30])[C:8](=[O:31])[C@H:7]2[CH2:32][CH3:33])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86668252HCID 86668252, compound

Product 1

HCID 68107395HCID 68107395, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

7-[[(7R)-8-Cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2-methyl-2,3-dihydrobenzofuran-4-carboxylate 30c (100 mg, 0.21 mmol) and 1 M lithium hydroxide solution were dissolved in 50 mL of the mixture solvent of methanol and tetrahydrofuran (V/V=1:1). The reaction solution was stirred for 12 hours followed by the addition of 1 M hydrochloric acid to adjust pH to 6 to 7. The resulting solution was concentrated under reduced pressure. The residue was added dropwise with 1 M lithium hydroxide solution to adjust pH to 3 to 4 and extracted with ethyl acetate (30 mL×3). The combined organic phase was concentrated under reduced pressure to obtain the title compound 7-[[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2-methyl-2,3-dihydrobenzofuran-4-carboxylic acid 30d (90 mg, yield: 95.0%) as a white solid.

Workup

  1. concentrationThe resulting solution was concentrated under reduced pressure
  2. additionThe residue was added dropwise with 1 M lithium hydroxide solution
  3. extractionextracted with ethyl acetate (30 mL×3)
  4. concentrationThe combined organic phase was concentrated under reduced pressure

Sources & evidence

ORD record
ord-92313759d9914912b6739bf63a6dcfc1
Source dataset
uspto-grants-2014_04
Patent number
US08691822B2

Reaction notes

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