Tetrahydrofuran → HCID 135759055, compound

HRID 750342Notes

Reaction equation

HRID 750342 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([NH:20][OH:21])=[NH:19])=[CH:16][CH:15]=1)[C:6]([C:24](=[O:27])[CH2:25][CH3:26])=[C:5]2[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C1CCN2C(=NCCC2)CC1.C1C[O:48][CH2:47]C1>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]3[NH:19][C:47](=[O:48])[O:21][N:20]=3)=[CH:16][CH:15]=1)[C:6]([C:24](=[O:27])[CH2:25][CH3:26])=[C:5]2[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178458125HCID 178458125, compound

Product 1

HCID 135759055HCID 135759055, compoundYield 48%

Conditions

Temperature
40 °C

Procedure

To a suspension of 4-(6-bromo-1-oxo-4-phenyl-3-propionyl-1H-isoquinolin-2-ylmethyl)-N-hydroxybenzamidine (230 mg) in THF (10 ml) was added 1,1′-carbodiimidazole (89 mg) and then 1,8-diazabicyclo[5.4.0]-7-undecene (0.08 ml) was added and the mixture was stirred at 40° C. for 15 hrs. The residue was partitioned between 1N hydrochloric acid and ethyl acetate. The organic layer was washed with brine and dried by adding sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1-+1/4) to give the title compound (102 mg, 48%).

Workup

  1. customThe residue was partitioned between 1N hydrochloric acid and ethyl acetate
  2. washThe organic layer was washed with brine
  3. customdried
  4. additionby adding sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1-+1/4

Sources & evidence

ORD record
ord-80ecf649dc734a0baf711481c048dad0
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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