Iodine → HCID 178452582, compound

HRID 1037388Notes

Reaction equation

HRID 1037388 reaction equation
[C:1]([O:5][C:6](=[O:38])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:19](=[O:37])[C:20]4[C:25]([O:26][C:27]=3[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[C:24]3[NH:34][N:35]=[CH:36][C:23]3=[CH:22][CH:21]=4)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].[I:41]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C=O)C>[C:1]([O:5][C:6](=[O:38])[NH:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[C:19](=[O:37])[C:20]4[C:25]([O:26][C:27]=3[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[C:24]3[NH:34][N:35]=[C:36]([I:41])[C:23]3=[CH:22][CH:21]=4)=[CH:16][CH:17]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 24477Sodium ThiosulfateHCID 67067899{1-[4-(6-Oxo-8-phenyl-1,6-dihydro-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-7-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Product 1

HCID 178452582HCID 178452582, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred ice-cooled solution of {1-[4-(6-oxo-8-phenyl-1,6-dihydro-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-7-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (52 mg, 0.10 mmol) in DMF (0.5 mL), was added powdered potassium hydroxide (45 mg, 0.80 mmol). After 3 min, a solution of iodine (102 mg, 0.40 mmol) in DMF (0.5 mL) was added. The resulting mixture was stirred at RT for 16 hours. Aqueous sodium thiosulfate was added and the mixture was extracted twice with EtOAc. The combined organic extracts were washed with water and brine, dried (Na2SO4), filtered and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 30 to 75% EtOAc in cyclohexane) to afford the title compound (4.2 mg, 7%) as a white solid. LCMS (Method H): RT=4.39 min, [M+H]+=634.

Workup

  1. extractionthe mixture was extracted twice with EtOAc
  2. washThe combined organic extracts were washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2e9b2aac6daa4d17be102c92f49ed7de
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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