Water → HCID 58052491, compound

HRID 2190208Notes

Reaction equation

HRID 2190208 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([C:11]1[N:16]=[C:15]2[O:17][C:18]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=3)=[C:19]([C:20]([NH:22][CH3:23])=[O:21])[C:14]2=[CH:13][C:12]=1[I:31])[S:7]([CH3:10])(=[O:9])=[O:8].C(N(CC)CC)C.S(=O)(=O)=O.N1C=CC=CC=1.O>CS(C)=O>[I:31][C:12]1[CH:13]=[C:14]2[C:19]([C:20]([NH:22][CH3:23])=[O:21])=[C:18]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=3)[O:17][C:15]2=[N:16][C:11]=1[N:6]([CH2:5][CH2:4][CH2:3][CH:2]=[O:1])[S:7]([CH3:10])(=[O:9])=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 168533Sulfur trioxide-pyridineHCID 58052386HCID 58052386, compound

Product 1

HCID 58052491HCID 58052491, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 6-(N-(4-hydroxybutyl)methylsulfonamido)-5-iodo-N-methyl-2-p-tolylfuro[2,3-b]pyridine-3-carboxamide (1 eq., 190 mg) in DMSO (1.7 ml) was added triethyl amine (8 eq., 0.38 ml) and pyridine sulfur trioxide (3 eq., 163 mg). The mixture was stirred at room temperature for 1 h. Water was added. The mixture was extracted with EtOAc. The organic layer was washed with water three times, dried over MgSO4 and concentrated to yield the crude title compound which was used in next step without purification.

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washThe organic layer was washed with water three times
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-36a55659990a427aaaa3bb3204ee1c89
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

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