Cyclopentanol → HCID 22724102, compound

HRID 2086876Notes

Reaction equation

HRID 2086876 reaction equation
[CH:1]1([OH:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.ClC(Cl)(O[C:11](=[O:17])OC(Cl)(Cl)Cl)Cl.[NH2:19][C:20]1[CH:21]=[C:22]([N:26]2[C:31](=[O:32])[C:30]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[N:29][C:28]3[CH:40]=[CH:41][CH:42]=[N:43][C:27]2=3)[CH:23]=[CH:24][CH:25]=1.C(=O)(O)[O-].[Na+]>ClCCCl.O1CCOCC1.C(N(CC)CC)C>[CH2:33]([C:30]1[C:31](=[O:32])[N:26]([C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([NH:19][C:11]([O:6][CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[O:17])[CH:21]=2)[C:27]2[N:43]=[CH:42][CH:41]=[CH:40][C:28]=2[N:29]=1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

8

Reactant 4

HCID 7298CyclopentanolHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 22724309HCID 22724309, compound

Product 1

HCID 22724102HCID 22724102, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 8471TriethylamineSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of cyclopentanol (0.08 ml) and triphosgene (87 mg) in 1,2-dichloroethane (2 ml) was stirred at room temperature for 20 hours. Then the mixture was added to a mixture of 4-(3-aminophenyl)-2-benzyl-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (193 mg) and triethylamine (0.25 ml) in 1,4-dioxane (3 ml). The mixture was stirred at room temperature for 1 hour, then poured into aqueous sodium bicarbonate and extracted with ethyl acetate twice. The combined organic phase was washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel column (chloroform-methanol, 40:1) to give 2-benzyl-4-(3-cyclopentyloxycarbonylaminophenyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (41 mg).

Workup

  1. stirringThe mixture was stirred at room temperature for 1 hour
  2. extractionextracted with ethyl acetate twice
  3. washThe combined organic phase was washed with aqueous sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel column (chloroform-methanol, 40:1)

Sources & evidence

ORD record
ord-b97d403dd9bc44a8a9d15c7f8629ebad
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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