Hydroxylamine → 7-(Pyridin-2-yl-quinolin-2-yl-amino)-heptanoic acid hydroxyamide

HRID 404140Notes

Reaction equation

HRID 404140 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:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1)[C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1)C>CN(C=O)C.CO>[OH:1][NH:2][C:6](=[O:5])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1)[C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1

Participants

5

Reactant 2

HCID 787HydroxylamineHCID 585450237-(Pyridin-2-yl-quinolin-2-yl-amino)-heptanoic acid ethyl ester

Product 1

HCID 468430527-(Pyridin-2-yl-quinolin-2-yl-amino)-heptanoic acid hydroxyamideYield 76%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

HONH2 (50% aqueous, 2 mL) was added to III (90 mg, 0.24 mmol) in DMF (0.5 mL) and MeOH (2 mL) at rt. The reaction mixture was stirred for 48 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 furnish IV as a colourless oil (66.43 mg, 76%).

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)

Sources & evidence

ORD record
ord-b759f961d010482fafe9cc922fbf89df
Source dataset
uspto-grants-2014_06
Patent number
US08748458B2

Reaction notes

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