HCID 89875789, compound → HCID 117952993, compound

HRID 1487039Notes

Reaction equation

HRID 1487039 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:22][CH:23]([CH3:25])[CH3:24])[S:10]([C:13]1[CH:21]=[CH:20][C:16]([C:17]([NH2:19])=O)=[CH:15][CH:14]=1)(=[O:12])=[O:11]>O1CCCC1>[NH2:19][CH2:17][C:16]1[CH:20]=[CH:21][C:13]([S:10]([N:9]([C:3]2[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=2[CH3:1])[CH2:22][CH:23]([CH3:25])[CH3:24])(=[O:12])=[O:11])=[CH:14][CH:15]=1

Participants

3

Reactant 1

HCID 89875789HCID 89875789, compound

Product 1

HCID 117952993HCID 117952993, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

4-(N-(2,4-dimethylphenyl)-N-isobutylsulfamoyl)benzamide (263.6 mg, 0.731 mmol) was dissolved in tetrahydrofuran (THF) (10 mL) and to this solution was added borane-tetrahydrofuran complex (1 M) (2.194 mL, 2.194 mmol). The reaction was then heated to 75° C. and refluxed overnight under nitrogen. The reaction was cooled and quenched by the addition of 2 M HCl. The reaction mixture was then neutralised by the slow addition of 10 M sodium hydroxide and the product extracted to the organic phase of an aqueous work up between ethyl acetate and water. The organic phase was passed through a hydrophobic frit and concentrated in vacuo. The crude was purified by mass directed autoprep (formic acid modifier), over 3 injections. The relevant fractions were evaporated in vacuo to give the required product, 152 mg. LCMS [LCMS1] Rt 0.87 min, m/z (ES+) 347 (M+H).

Workup

  1. additionwas added borane-tetrahydrofuran complex (1 M) (2.194 mL, 2.194 mmol)
  2. temperaturerefluxed overnight under nitrogen
  3. temperatureThe reaction was cooled
  4. customquenched by the addition of 2 M HCl
  5. additionThe reaction mixture was then neutralised by the slow addition of 10 M sodium hydroxide
  6. extractionthe product extracted to the organic phase of an aqueous work up between ethyl acetate and water
  7. concentrationconcentrated in vacuo
  8. customThe crude was purified by mass
  9. customThe relevant fractions were evaporated in vacuo

Sources & evidence

ORD record
ord-3510accdcb4f4325bbfb6a3fc484bbe2
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

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