Hydrochloric Acid → 3-cyclopropyl-1-[1-(3-[1,2,4]oxadiazol-3-yl-propyl)-1H-benzoimidazol-2-ylmethyl]-1H-quinazoline-2,4-dione

HRID 1835839Notes

Reaction equation

HRID 1835839 reaction equation
[CH:1]1([N:4]2[C:13](=[O:14])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][C:5]2=[O:15])[CH2:3][CH2:2]1.CC(N=P(N1CCCC1)(N1CCCC1)N1CCCC1)(C)C.Cl[CH2:38][C:39]1[N:43]([CH2:44][CH2:45][CH2:46][C:47]2[N:51]=[CH:50][O:49][N:48]=2)[C:42]2[CH:52]=[CH:53][CH:54]=[CH:55][C:41]=2[N:40]=1.Cl>CN(C=O)C>[CH:1]1([N:4]2[C:13](=[O:14])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[N:6]([CH2:38][C:39]3[N:43]([CH2:44][CH2:45][CH2:46][C:47]4[N:51]=[CH:50][O:49][N:48]=4)[C:42]4[CH:52]=[CH:53][CH:54]=[CH:55][C:41]=4[N:40]=3)[C:5]2=[O:15])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3856267tert-Butylimino-tri(pyrrolidino)phosphoraneHCID 172214493-cyclopropyl-1H-quinazoline-2,4-dioneHCID 225958052-chloromethyl-1-(3-[1,2,4]oxadiazol-3-yl-propyl)-1H-benzoimidazole

Product 1

HCID 235170683-cyclopropyl-1-[1-(3-[1,2,4]oxadiazol-3-yl-propyl)-1H-benzoimidazol-2-ylmethyl]-1H-quinazoline-2,4-dioneYield 14%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-cyclopropyl-1H-quinazoline-2,4-dione, 159a, (83 mg, 0.41 mmol) in DMF (6 mL) was added BTPP (269 mg, 0.86 mmol) and the solution was stirred for 15 min. 2-Chloromethyl-1-(3-[1,2,4]oxadiazol-3-yl-propyl)-1H-benzoimidazole, 205, HCl salt (128 mg, 0.41 mmol) was added and stirring was continued for 1 h. The solution was concentrated and water was added to the residue. The white precipitate was collected by filtration, washed with water and purified by flash chromatography (eluent dichloromethane-ethyl acetate 2:1, 1:1) to afford 3-cyclopropyl-1-[1-(3-[1,2,4]oxadiazol-3-yl-propyl)-1H-benzoimidazol-2-ylmethyl]-1H-quinazoline-2,4-dione (26 mg, 14%) as a white solid:

Workup

  1. stirringstirring
  2. waitwas continued for 1 h
  3. concentrationThe solution was concentrated
  4. additionwater was added to the residue
  5. filtrationThe white precipitate was collected by filtration
  6. washwashed with water
  7. custompurified by flash chromatography (eluent dichloromethane-ethyl acetate 2:1, 1:1)

Sources & evidence

ORD record
ord-212f1ca2d2b947dfa663068a73a318eb
Source dataset
uspto-grants-2004_08
Patent number
US06774134B2

Reaction notes

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