Hydroxylamine → cis-N-hydroxy-6-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclohex-3-ene-1-carboxamide

HRID 736707Notes

Reaction equation

HRID 736707 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([S:20]([NH:23][C@@H:24]3[C@H:29]([C:30]([OH:32])=O)[CH2:28][CH:27]=[CH:26][CH2:25]3)(=[O:22])=[O:21])=[CH:16][CH:15]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[OH:33][N:34]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.NO>CN(C)C=O>[OH:33][NH:34][C:30]([C@H:29]1[C@@H:24]([NH:23][S:20]([C:17]2[CH:16]=[CH:15][C:14]([O:13][CH2:12][C:10]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[N:3]=[C:2]([CH3:1])[CH:11]=3)=[CH:19][CH:18]=2)(=[O:21])=[O:22])[CH2:25][CH:26]=[CH:27][CH2:28]1)=[O:32]

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68819512cis-6-[({4-[(2-Methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclohex-3-ene-1-carboxylic acid

Product 1

HCID 86607866cis-N-hydroxy-6-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclohex-3-ene-1-carboxamideYield 38.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 181.0 mg (0.4 mmol) of cis-6-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclohex-3-ene-1-carboxylic acid and 162.2 mg (1.2 mmol) of 1-hydroxybenzotriazole in 3 mL of N,N-dimethylformamide at 0° C. was added 230.0 mg (1.2 mmol) of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride. The reaction mixture was stirred at room temperature for 1.5 h. To the reaction mixture at 0° C. was added 0.2 mL of 50% hydroxylamine solution. The resulting reaction mixture was stirred at room temperature for 18 h. The volatile materials were removed under reduced pressure, below 40° C. The residue was dissolved in 80 mL of ethyl acetate. The organic layer was washed with a saturated sodium bicarbonate solution (5×30 mL) and a saturated sodium chloride solution (2×30 mL) and dried over sodium sulfate. After removal of the ethyl acetate, the residue was triturated with a 7:3 mixture of hexane:ethyl acetate to give 71.9 mg of cis-N-hydroxy-6-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclohex-3-ene-1-carboxamide as a solid in 38% yield. MS: 468.1 (M+H)+

Workup

  1. customThe resulting reaction mixture
  2. stirringwas stirred at room temperature for 18 h
  3. customThe volatile materials were removed under reduced pressure, below 40° C
  4. dissolutionThe residue was dissolved in 80 mL of ethyl acetate
  5. washThe organic layer was washed with a saturated sodium bicarbonate solution (5×30 mL)
  6. dry with materiala saturated sodium chloride solution (2×30 mL) and dried over sodium sulfate
  7. customAfter removal of the ethyl acetate
  8. customthe residue was triturated with a 7:3 mixture of hexane

Sources & evidence

ORD record
ord-a2c1869c294f4061bd8dc2e4709ea7ae
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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