Ethanol → HCID 67280049, compound

HRID 1693328Notes

Reaction equation

HRID 1693328 reaction equation
FC(F)(F)S(O[C:7]1[C:16]2[CH2:15][S:14][N:13]=[C:12]([N:17]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:11]3=[N:32][N:33]([CH2:35][C:36]4[C:41]([CH3:42])=[C:40]([O:43][CH3:44])[C:39]([CH3:45])=[CH:38][N:37]=4)[N:34]=[C:9]([C:10]=23)[CH:8]=1)(=O)=O.C(N([CH2:53][CH3:54])CC)C.[C]=[O:56].[CH2:57]([OH:59])C>C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:28]([O:27][C:25]([N:17]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[C:12]1[C:11]2[C:10]3[C:9](=[N:34][N:33]([CH2:35][C:36]4[C:41]([CH3:42])=[C:40]([O:43][CH3:44])[C:39]([CH3:45])=[CH:38][N:37]=4)[N:32]=2)[CH:8]=[C:7]([C:57]([O:59][CH2:53][CH3:54])=[O:56])[C:16]=3[CH2:15][S:14][N:13]=1)=[O:26])([CH3:30])([CH3:29])[CH3:31]

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 86641355HCID 86641355, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 67280049HCID 67280049, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 178419050HCID 178419050, compoundCatalyst

Procedure

4-[Bis(tert-butoxycarbonyl)amino]-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-2,7-dihydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-8-yl trifluoromethanesulfonate (25 mg) was dissolved in ethanol (2 ml). Triethylamine (6 μl) and bis(triphenylphosphine)palladium (II) dichloride (2.5 mg) were added at room temperature, and the mixture was stirred in a carbon monoxide atmosphere at 40° C. for three hours. The reaction solution was concentrated, and the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain the title compound as an oil (14 mg, 62%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. customthe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-296f837d3d03403c89542eaae33d1729
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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