Hydroxylamine → HCID 44182594, compound

HRID 878477Notes

Reaction equation

HRID 878477 reaction equation
[CH:1]1([N:4]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[N:6]=[C:5]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21]C)=O)[CH2:3][CH2:2]1.[NH2:23][OH:24].[OH-].[K+]>C1COCC1>[CH:1]1([N:4]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[N:6]=[C:5]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([NH:23][OH:24])=[O:21])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 14797Potassium HydroxideHCID 66777345HCID 66777345, compound

Product 1

HCID 44182594HCID 44182594, compoundYield 63.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 7-(1-cyclopropyl-1H-benzo[d]imidazol-2-yl)heptanoate (80 mg, 0.27 mmol) in THF at 0° C. was added 50% hydroxylamine solution (0.16 mL, 2.6 mmol). To this was added KOH (0.80 mL, 1M in MeOH, 0.80 mmol) dropwise. The reaction was stirred at 0° C. for 2 hr, briefly concentrated and neutralized by adding 1 N HCl solution until pH was 7. The mixture was extracted with ethyl acetate, dried and concentrated. The residue was purified by biotage column chromatography to give 7-(1-cyclopropyl-1H-benzo[d]imidazol-2-yl)-N-hydroxyheptanamide 24 (52 mg). MS (M+1=302)

Workup

  1. concentrationbriefly concentrated
  2. additionby adding 1 N HCl solution until pH was 7
  3. extractionThe mixture was extracted with ethyl acetate
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by biotage column chromatography

Sources & evidence

ORD record
ord-15879c9801ea47f999d57b3eb7708eb3
Source dataset
uspto-grants-2015_03
Patent number
US08987468B2

Reaction notes

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