Tetrahydrofuran → HCID 68699889, compound

HRID 2352983Notes

Reaction equation

HRID 2352983 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[C:5]([C:7]1[CH:15]=[C:14]2[C:10]([CH2:11][C:12](=[O:16])[NH:13]2)=[CH:9][CH:8]=1)=[O:6].[CH3:20][N:21]1[C:25]([CH:26]=O)=[CH:24][CH:23]([CH3:28])[NH:22]1.C([BH3-])#N.[Na+].C1COCC1>O.C(O)(=O)C>[CH3:20][N:21]1[C:25]([CH2:26][NH:1][C:2]2[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=2)[C:5]([C:7]2[CH:15]=[C:14]3[C:10]([CH2:11][C:12](=[O:16])[NH:13]3)=[CH:9][CH:8]=2)=[O:6])=[CH:24][C:23]([CH3:28])=[N:22]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 5003444Sodium cyanoborohydrideHCID 592564786-(3-Amino-benzoyl)-1,3-dihydro-indol-2-oneHCID 86610473HCID 86610473, compound

Product 1

HCID 68699889HCID 68699889, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A dry round bottom flask was charged with 6-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one (as prepared in Example 40, 0.300 g, 1.19 mmol), 1,3-Dimethyl-2H-pyrazole-5-carbaldehyde (0.191 g, 1.91 mmol) and acetic acid (0.3 mL). The mixture was allowed to stir for 4 h at room temperature. A 1M solution of sodium cyanoborohydride in THF (3.57 mL, 3.57 mmol) was then added and the mixture was allowed to stir for 45 minutes. The reaction mixture was poured into H2O (100 mL) and allowed to stir for 15 minutes. The resulting suspension was vacuum filtered and the filtrate was extracted with EtOAc (3ט100 mL). The organic layers were combined, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to afford a yellow oil. The yellow oil was then chromatographed over silica which had been previously neutralized by flushing the column with the purification eluant (97/3, chloroform/methanol w/0.5% NEt3) several times. This chromatographic purification resulted in the isolation of pure 6-{3-[(2,5-Dimethyl-2H-pyrazol-3-ylmethyl)-amino]-benzoyl}-1,3-dihydro-indol-2-one in 30% yield (0.128 g, 0.357 mmol).

Workup

  1. stirringto stir for 45 minutes
  2. stirringto stir for 15 minutes
  3. filtrationfiltered
  4. extractionthe filtrate was extracted with EtOAc (3ט100 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford a yellow oil
  9. customThe yellow oil was then chromatographed over silica which
  10. customby flushing the column with the purification eluant (97/3, chloroform/methanol w/0.5% NEt3) several times
  11. customThis chromatographic purification

Sources & evidence

ORD record
ord-1b67ea1bd3964d0fb1c83764ce1ef2ec
Source dataset
uspto-grants-2010_07
Patent number
US07749530B2

Reaction notes

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