Hydroxylamine → 7-((5-(Benzyloxy)pyridin-2-yl)(pyridin-2-yl)amino)-n-hydroxyheptanamide

HRID 523910Notes

Reaction equation

HRID 523910 reaction equation
[OH:1][NH2:2].C([O:5][C:6](=O)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:22][N:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)C>CN(C=O)C.CO>[CH2:27]([O:26][C:23]1[CH:24]=[CH:25][C:20]([N:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]([NH:2][OH:1])=[O:5])=[N:21][CH:22]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 2

HCID 787HydroxylamineHCID 585450367-[(5-Benzyloxy-pyridin-2-yl)-pyridin-2-yl-amino]heptanoic acid ethyl ester

Product 1

HCID 468524567-((5-(Benzyloxy)pyridin-2-yl)(pyridin-2-yl)amino)-n-hydroxyheptanamideYield 74%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

HONH2 (50% aqueous, 0.5 mL) was added to III (26 mg, 0.06 mmol) in DMF (0.2 mL) and MeOH (0.5 mL) at rt. The reaction mixture was stirred for 72 h, after which the solvents were evaporated under reduced pressure. The resulting residue was dissolved and co-evaporated with toluene (2×10 mL) then was purified by silica gel column chromatography eluting with CH2Cl2/MeOH (100:4 to 100:8) to furnish IV as a colourless oil (18.66 mg, 74%).

Workup

  1. customafter which the solvents were evaporated under reduced pressure
  2. dissolutionThe resulting residue was dissolved
  3. customthen was purified by silica gel column chromatography
  4. washeluting with CH2Cl2/MeOH (100:4 to 100:8)

Sources & evidence

ORD record
ord-dfa97aca836b440fa79a391daed0141b
Source dataset
uspto-grants-2016_05
Patent number
US09340503B2

Reaction notes

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