Water → HCID 58656520, compound

HRID 1988940Notes

Reaction equation

HRID 1988940 reaction equation
[CH:1]1([NH:4][C:5](=[O:23])[C:6]2[CH:11]=[C:10]([C:12]3[CH:13]=[C:14]4[C:18](=[CH:19][CH:20]=3)[NH:17][N:16]=[CH:15]4)[C:9]([CH3:21])=[C:8]([F:22])[CH:7]=2)[CH2:3][CH2:2]1.[H-].[Na+].Br[CH2:27][C:28]([O:30][CH3:31])=[O:29].O>CN(C=O)C>[CH:1]1([NH:4][C:5]([C:6]2[CH:7]=[C:8]([F:22])[C:9]([CH3:21])=[C:10]([C:12]3[CH:13]=[C:14]4[C:18](=[CH:19][CH:20]=3)[N:17]([CH2:27][C:28]([O:30][CH3:31])=[O:29])[N:16]=[CH:15]4)[CH:11]=2)=[O:23])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 10403067N-Cyclopropyl-3-fluoro-5-(1H-indazol-5-yl)-4-methylbenzamide

Product 1

HCID 58656520HCID 58656520, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of N-cyclopropyl-3-fluoro-5-(1H-indazol-5-yl)-4-methylbenzamide (example 60) (0.35 g) in dry DMF (5 ml) was treated with sodium hydride (60% oil dispersion, 0.08 g) at room temp under nitrogen then stirred for 20 min. A solution of methyl bromoacetate (0.2 ml) in dry DMF (0.5 ml) was added and stirring was continued for 1 h. Water (30 ml) was added and the mixture was extracted with ethyl acetate (×2). The organic extracts were washed with water (×3) and brine, dried (Na2SO4) and concentrated under vacuum. The residue was purified using a Varian Bond-Elut SPE cartridge (silica, 10 g) eluting with cyclohexane:ethyl acetate (4:1 to 1:1) to give the title compound as a yellow foam (0.26 g).

Workup

  1. stirringstirring
  2. waitwas continued for 1 h
  3. extractionthe mixture was extracted with ethyl acetate (×2)
  4. washThe organic extracts were washed with water (×3) and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified
  8. washeluting with cyclohexane:ethyl acetate (4:1 to 1:1)

Sources & evidence

ORD record
ord-3b6e72546b584b87a730c6b92be46d34
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

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