Dichloromethane → 3-{4-[4-(Tetrahydro-furan-2-carbonyl)-piperazine-1-carbonyl]-cyclohexyl methyl}-1H-quinazoline-2,4-dione

HRID 538043Notes

Reaction equation

HRID 538043 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6]([OH:8])=O.C(Cl)Cl.[N:12]1([C:18]([C@H:20]2[CH2:25][CH2:24][C@H:23]([CH2:26][N:27]3[C:36](=[O:37])[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[NH:29][C:28]3=[O:38])[CH2:22][CH2:21]2)=[O:19])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1>>[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6]([N:15]1[CH2:16][CH2:17][N:12]([C:18]([CH:20]2[CH2:25][CH2:24][CH:23]([CH2:26][N:27]3[C:36](=[O:37])[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[NH:29][C:28]3=[O:38])[CH2:22][CH2:21]2)=[O:19])[CH2:13][CH2:14]1)=[O:8]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 86079(+-)-Tetrahydro-2-furoic acidHCID 178518590HCID 178518590, compound

Product 1

HCID 671148553-{4-[4-(Tetrahydro-furan-2-carbonyl)-piperazine-1-carbonyl]-cyclohexyl methyl}-1H-quinazoline-2,4-dioneYield 55.3%

Procedure

To a suspension of tetrahydro-2-furoic acid (38 mg, 0.32 mmol) in DCM (3 mL) 1,1-carbonyldiimidazole (52 mg, 0.32 mmol) was added and the mixture was stirred for 6 hours at room temperature. Then 3-[trans-4-(piperazine-1-carbonyl)-cyclohexylmethyl]-1H-quinazoline-2,4-dione (100 mg, 0.27 mmol) was added and the reaction left stirring for 18 hours. The mixture was washed with 0.4 M Na2CO3 solution and the organic phase collected and concentrated under reduced pressure. The crude was purified by silica column eluting with DCM:MeOH (98:2). 70 mg of the titled compound were obtained (yield 55%).

Workup

  1. additionwas added
  2. waitthe reaction left
  3. stirringstirring for 18 hours
  4. washThe mixture was washed with 0.4 M Na2CO3 solution
  5. customthe organic phase collected
  6. concentrationconcentrated under reduced pressure
  7. customThe crude was purified by silica column
  8. washeluting with DCM:MeOH (98:2)

Sources & evidence

ORD record
ord-51d03941e4d848abb5705b63a883cc81
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Reaction notes

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