Iodine → {1-[4-(1-Methyl-6-oxo-8-phenyl-1,6-dihydro-chromeno[7,8-d]imidazol-7-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

HRID 1037385Notes

Reaction equation

HRID 1037385 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:27](=[O:28])[C:26]4[C:21](=[C:22]([NH:30][CH3:31])[C:23]([NH2:29])=[CH:24][CH:25]=4)[O:20][C:19]=3[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:39]OC(OC)OC.II>C(#N)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:27](=[O:28])[C:26]4[CH:25]=[CH:24][C:23]5[N:29]=[CH:31][N:30]([CH3:39])[C:22]=5[C:21]=4[O:20][C:19]=3[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:16][CH:17]=2)[CH2:9][CH2:10][CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 807IodineHCID 9005Trimethyl orthoformateHCID 67067881{1-[4-(7-Amino-8-methylamino-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl)-carbamic acid tert-butyl ester

Product 1

HCID 68227562{1-[4-(1-Methyl-6-oxo-8-phenyl-1,6-dihydro-chromeno[7,8-d]imidazol-7-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl esterYield 68%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of {1-[4-(7-amino-8-methylamino-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (95 mg, 0.19 mmol) in acetonitrile (3 mL) was added trimethylorthoformate (24 μL, 0.22 mmol) and iodine (5 mg, 0.02 mmol) at RT. After 1 hour, the reaction mixture was quenched with Na2S2O3. The resulting mixture was extracted with ethyl acetate (2×30 mL) and the combined organics washed with brine, dried (Na2SO4) and the solvents were removed in vacuo. The resulting residue was subjected to flash chromatography (SiO2, ethyl acetate) to give the title compound as a white solid (67 mg, 68%). LCMS (Method G): RT=3.63 min, [M+H]+=522.

Workup

  1. customthe reaction mixture was quenched with Na2S2O3
  2. extractionThe resulting mixture was extracted with ethyl acetate (2×30 mL)
  3. washthe combined organics washed with brine
  4. dry with materialdried (Na2SO4)
  5. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-6cb188d5ebe04cfdbab57032e2663913
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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