1,1'-Carbonyldiimidazole → HCID 54559816, compound

HRID 863500Notes

Reaction equation

HRID 863500 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[NH2:30][CH:31]1[CH2:45][C:34]2[C:35]3[NH:36][C:37](=[O:44])[C:38](=[O:43])[NH:39][C:40]=3[CH:41]=[CH:42][C:33]=2[CH2:32]1>O1CCCC1>[C:4]([O:3][C:1]([N:8]1[CH2:9][CH2:10][CH:11]([C:14](=[O:16])[NH:30][CH:31]2[CH2:45][C:34]3[C:35]4[NH:36][C:37](=[O:44])[C:38](=[O:43])[NH:39][C:40]=4[CH:41]=[CH:42][C:33]=3[CH2:32]2)[CH2:12][CH2:13]1)=[O:2])([CH3:5])([CH3:6])[CH3:7]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 19696185HCID 19696185, compound

Product 1

HCID 54559816HCID 54559816, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of N-Boc-piperidine-4-carboxylic acid (0.23 g, 1 mmol) and 1,1'-carbonyldiimidazole (0.16 g, 1 mmol) in tetrahydrofuran (5 mL) was heated at 80° C. for 15 min. After cooling, it was added to a solution of 8-amino-4,7,8,9-tetrahydro-1H-cyclopenta[f]quinoxaline-2,3-dione hydrochloride (0.11 g, 0.5 mmol) and the mixture was heated at 70° C. for 2 days. After filtration to remove precipitate, the filtrate was evaporated and the residue suspended in water. The resulting solid was collected by filtration, washed with diethyl and dried in vacuo (0.15 g, 70% yield).

Workup

  1. temperatureAfter cooling
  2. temperaturethe mixture was heated at 70° C. for 2 days
  3. filtrationAfter filtration
  4. customto remove precipitate
  5. customthe filtrate was evaporated
  6. filtrationThe resulting solid was collected by filtration
  7. washwashed with diethyl
  8. customdried in vacuo (0.15 g, 70% yield)

Sources & evidence

ORD record
ord-b34aa1eeb3da4d138021a5c26854f90a
Source dataset
uspto-grants-1998_02
Patent number
US05721234

Reaction notes

Loading…