Hydroxylamine → HCID 21919395, compound

HRID 1581941Notes

Reaction equation

HRID 1581941 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14](/[CH:17]=[CH:18]/[CH2:19][CH2:20][C:21]3[N:26]=[CH:25][C:24]([F:27])=[CH:23][N:22]=3)(=[O:16])=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.ClC1C=CC(N2CCN(S(/C=C\CCC3N=CC(F)=CN=3)(=O)=O)CC2)=NC=1.[NH2:55][OH:56]>O1CCCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([CH2:17][CH:18]([NH:55][OH:56])[CH2:19][CH2:20][C:21]3[N:26]=[CH:25][C:24]([F:27])=[CH:23][N:22]=3)(=[O:16])=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 787HydroxylamineHCID 21919407HCID 21919407, compoundHCID 69596186HCID 69596186, compound

Product 1

HCID 21919395HCID 21919395, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-((E)-4-[4-(5-chloropyridin-2-yl)piperazino]sulfonylbut-3-enyl)-5-fluoropyrimidine and 2-((Z)-4-[4-(5-chloropyridin-2-yl)piperazino]sulfonylbut-3-enyl)-5-fluoropyrimidine (0.44 g), in tetrahydrofuran (5 ml), was added hydroxylamine (1.0 ml, 50% aqueous solution). The mixture was stirred for 18 hours and then diluted with EtOAc (10 ml) and washed with saturated ammonium chloride solution (10 ml). The organic layer was dried over Na2SO4 and evaporated in vacuo to give 2-[4-[4-(5-chloropyridin-2-yl)piperazino]sulfonyl-3-(hydroxyamino)butyl]-5-fluoropyrimidine (0.483 g).

Workup

  1. washwashed with saturated ammonium chloride solution (10 ml)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-8661a4b06e844750b1220944b21e3145
Source dataset
uspto-grants-2004_05
Patent number
US06734183B2

Reaction notes

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