Ethanol → HCID 68830197, compound

HRID 1819292Notes

Reaction equation

HRID 1819292 reaction equation
[OH-].[Na+:2].C(O)C.O1CCCC1.Cl.[NH2:12][C@@H:13]1[CH2:18][CH2:17][CH2:16][N:15]([C:19]2[N:27]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[Cl:35])[C:26]3[C:25](=[O:36])[N:24]([CH3:37])[C:23](=[O:38])[N:22]([CH3:39])[C:21]=3[C:20]=2[C:40]([O:42]C)=[O:41])[CH2:14]1>O>[NH2:12][C@@H:13]1[CH2:18][CH2:17][CH2:16][N:15]([C:19]2[N:27]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[Cl:35])[C:26]3[C:25](=[O:36])[N:24]([CH3:37])[C:23](=[O:38])[N:22]([CH3:39])[C:21]=3[C:20]=2[C:40]([O-:42])=[O:41])[CH2:14]1.[Na+:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 68829769HCID 68829769, compound

Product 1

HCID 68830197HCID 68830197, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A 1N aqueous sodium hydroxide solution (1 ml), ethanol (1 ml) and tetrahydrofuran (1 ml) were added to methyl 6-[(3R)-3-aminopiperidin-1-yl]-5-(2-chlorobenzyl)-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidine-7-carboxylate hydrochloride (53 mg), and the resulting mixture was stirred at 80° C. for 3 hours. After the reaction solution was cooled to 25° C., water was added thereto, followed by washing with ethyl acetate, and the aqueous layer was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and filtered and the filtrate was concentrated under reduced pressure to obtain the title compound (41 mg) as a white solid.

Workup

  1. temperatureAfter the reaction solution was cooled to 25° C.
  2. washby washing with ethyl acetate
  3. extractionthe aqueous layer was extracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5c7c6d7b54df4ae29ce48ee6b84aaab4
Source dataset
uspto-grants-2009_10
Patent number
US07601728B2

Reaction notes

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