Hydroxylamine → HCID 86607871, compound

HRID 736723Notes

Reaction equation

HRID 736723 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[CH2:28][N:27]([S:29]([CH3:32])(=[O:31])=[O:30])[CH2:26][C@H:25]3[C:33]([OH:35])=O)(=[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:36][N:37]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.NO>CN(C)C=O>[OH:36][NH:37][C:33]([C@H:25]1[C@@H:24]([NH:23][S:20]([C:17]2[CH:18]=[CH:19][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:15][CH:16]=2)(=[O:22])=[O:21])[CH2:28][N:27]([S:29]([CH3:32])(=[O:30])=[O:31])[CH2:26]1)=[O:35]

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68817296HCID 68817296, compound

Product 1

HCID 86607871HCID 86607871, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 152 mg (0.24 mmol) of cis-4-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]-1-(methylsulfonyl)pyrrolidine-3-carboxylic acid and 97.3 mg (0.72 mmol) of 1-hydroxybenzotriazole in 3 mL of N,N-dimethylformamide at 0° C. was added 138 mg (0.72 mmol) of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride. The reaction mixture was stirred at room temperature for 1.5 h. To the 0° C. reaction mixture was added 0.12 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), dried over sodium sulfate and filtered. After removal of the ethyl acetate, the residue was triturated with a 7:3 hexane:ethyl acetate mixture to give 114.1 mg of cis-N-hydroxy-4-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]-1-(methylsulfonyl)pyrrolidine-3-carboxamide as a yellow solid in 89% yield. MS: 535.2 (M+H)+

Workup

  1. customTo the 0° C. reaction mixture
  2. customThe resulting reaction mixture
  3. stirringwas stirred at room temperature for 18 h
  4. customThe volatile materials were removed under reduced pressure below 40° C
  5. dissolutionThe residue was dissolved in 80 mL of ethyl acetate
  6. washThe organic layer was washed with a saturated sodium bicarbonate solution (5×30 mL)
  7. dry with materiala saturated sodium chloride solution (2×30 mL), dried over sodium sulfate
  8. filtrationfiltered
  9. customAfter removal of the ethyl acetate
  10. customthe residue was triturated with a 7:3 hexane

Sources & evidence

ORD record
ord-c563d201f28f48a9b24d273629d2d237
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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