1,8-Diazabicyclo(5.4.0)undec-7-ene → 6-bromo-N-cyclopropyl-1,2-benzisoxazol-3-amine

HRID 1988897Notes

Reaction equation

HRID 1988897 reaction equation
N12CCCN=C1CCCCC2.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[N:24][OH:25])[NH:20][CH:21]2[CH2:23][CH2:22]2)=[C:15](F)[CH:14]=1>O1CCCC1>[Br:12][C:13]1[CH:18]=[CH:17][C:16]2[C:19]([NH:20][CH:21]3[CH2:23][CH2:22]3)=[N:24][O:25][C:15]=2[CH:14]=1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 1785263504-Bromo-N-cyclopropyl-2-fluoro-N'-hydroxybenzenecarboximidamide2×

Product 1

HCID 591273806-bromo-N-cyclopropyl-1,2-benzisoxazol-3-amineYield 70.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,8-Diazabicyclo[5.4.0]undec-7-ene (0.12 ml) was added to 4-bromo-N-cyclopropyl-2-fluoro-N′-hydroxybenzenecarboximidamide (Intermediate 52) (0.2 g) in tetrahydrofuran (2 ml) then heated at 150° in a microwave for 70 min. The mixture was applied to a Varian Bond-Elut SPE cartridge (silica, 20 g) then eluted with cyclohexane:ethyl acetate (100:0 to 80:20) to give the title compound as a white solid (0.13 g).

Workup

  1. temperaturethen heated at 150° in a microwave for 70 min
  2. washthen eluted with cyclohexane:ethyl acetate (100:0 to 80:20)

Sources & evidence

ORD record
ord-c25a435f6b26479aac368fa367a32617
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

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