Water → HCID 66953519, compound

HRID 2096979Notes

Reaction equation

HRID 2096979 reaction equation
N12CCCN=C1CCCCC2.F[C:13]1[C:31]([I:32])=[C:30]([CH3:33])[CH:29]=[CH:28][C:14]=1[C:15](=[N:26][OH:27])[NH:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1.O>O1CCCC1>[I:32][C:31]1[C:13]2[O:27][N:26]=[C:15]([NH:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[C:14]=2[CH:28]=[CH:29][C:30]=1[CH3:33]

Participants

5

Reactant 3

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178491142HCID 178491142, compound

Product 1

HCID 66953519HCID 66953519, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,8-Diazabicyclo[5.4.0]undec-7-ene (0.31 mL, 2.0 mmol) was added dropwise to a solution of 2-fluoro-N′-hydroxy-3-iodo-N-(4-methoxybenzyl)-4-methylbenzimidamide (preparation 23a, 0.80 g, 1.9 mmol) in tetrahydrofuran (10 mL). The mixture was then heated under microwave conditions (“Initiator sixty” from Biotage®) at 150° C. for 4 hours under an argon atmosphere. The mixture was then poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and evaporated. The residue was purified by flash chromatography (10:1 to 4:1 hexanes/ethyl acetate) to give the title compound (0.29 g, 38%) as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by flash chromatography (10:1 to 4:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-96800e36c02245e09e25639bcf089664
Source dataset
uspto-grants-2013_05
Patent number
US08450341B2

Reaction notes

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