Iodine → HCID 178432084, compound

HRID 1037365Notes

Reaction equation

HRID 1037365 reaction equation
[C:1]([O:5][C:6](=[O:37])[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]([NH2:30])[C:23]([NH2:29])=[CH:24][CH:25]=4)[O:20][C:19]=3[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:38][C:39](C)(C)C([O-])([O-])[O-].II>CC#N>[C:1]([O:5][C:6](=[O:37])[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]=[C:38]([CH3:39])[NH:30][C:22]=5[C:21]=4[O:20][C:19]=3[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)=[CH:16][CH:17]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 807Iodine2×HCID 21927715Trimethylorthoacetate2×HCID 67067961{1-[4-(7,8-diamino-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Product 1

HCID 178432084HCID 178432084, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of {1-[4-(7,8-diamino-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (80 mg, 0.16 mmol) in CH3CN (8 mL) was added trimethylorthoacetate (25 μL, 0.20 mmol) and iodine (4 mg, 0.016 mmol) and the reaction mixture was stirred at RT for 2.5 hours. Further trimethylorthoacetate (50 μL, 0.40 mmol) and iodine (24 mg, 0.096 mmol) were added and the reaction stirred for 1 hour. The reaction was quenched with aqueous Na2S2O3, diluted with ethyl acetate and the phases separated. The organic extracts were washed with brine, dried (NaSO4), filtered 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 brown solid (35 mg, 42%). LCMS (Method G): RT=3.18 min, [M+H]+=522.

Workup

  1. stirringthe reaction stirred for 1 hour
  2. customThe reaction was quenched with aqueous Na2S2O3
  3. additiondiluted with ethyl acetate
  4. customthe phases separated
  5. washThe organic extracts were washed with brine
  6. dry with materialdried (NaSO4)
  7. filtrationfiltered
  8. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-a8b7a31d68b84dbcbb39c1941961fb54
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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