Water → HCID 57789974, compound

HRID 1819321Notes

Reaction equation

HRID 1819321 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[N:23]([CH2:24][C:25]3[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=3[Cl:32])[C:22]3[C:21](=[O:33])[NH:20][C:19](=[O:34])[N:18]([CH3:35])[C:17]=3[C:16]=2[C:36]([O:38][CH3:39])=[O:37])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:41][C:42]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[O:43].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[N:23]([CH2:24][C:25]3[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=3[Cl:32])[C:22]3[C:21](=[O:33])[N:20]([CH2:41][C:42](=[O:43])[C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[C:19](=[O:34])[N:18]([CH3:35])[C:17]=3[C:16]=2[C:36]([O:38][CH3:39])=[O:37])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6259Phenacyl bromideHCID 11430Potassium CarbonateHCID 57886945HCID 57886945, compound

Product 1

HCID 57789974HCID 57789974, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 6-{(3R)-3-[(tertbutoxycarbonyl)amino]piperidin-1-yl}-5-(2-chloro-5-fluorobenzyl)-1-methyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidine-7-carboxylate (50 mg), α-bromoacetophenone (27 mg) and potassium carbonate (25 mg) in N,N-dimethylformamide was stirred at 25° C. for 14 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and then filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by a preparative thin-layer chromatography (hexane/ethyl acetate=2/1) to obtain the title compound (51 mg) as a white solid.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by a preparative thin-layer chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-2604c4d2109c4c6f9619ab1ee9a1dc2b
Source dataset
uspto-grants-2009_10
Patent number
US07601728B2

Reaction notes

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