Hydroxylamine → HCID 11705851, compound

HRID 1723815Notes

Reaction equation

HRID 1723815 reaction equation
[F:1][C:2]([F:31])([F:30])[CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:16][CH2:15][N:14]([S:17](/[CH:20]=[CH:21]/[CH2:22][CH2:23][C:24]3[N:29]=[CH:28][CH:27]=[CH:26][N:25]=3)(=[O:19])=[O:18])[CH2:13][CH2:12]2)=[N:9][CH:10]=1.[NH2:32][OH:33].O>C1COCC1>[OH:33][NH:32][CH:21]([CH2:20][S:17]([N:14]1[CH2:13][CH2:12][N:11]([C:8]2[CH:7]=[CH:6][C:5]([O:4][CH2:3][C:2]([F:30])([F:1])[F:31])=[CH:10][N:9]=2)[CH2:16][CH2:15]1)(=[O:19])=[O:18])[CH2:22][CH2:23][C:24]1[N:29]=[CH:28][CH:27]=[CH:26][N:25]=1

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 962WaterHCID 68849360HCID 68849360, compound

Product 1

HCID 11705851HCID 11705851, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-[(3E)-4-({4-[5-(2,2,2-trifluoroethoxy)pyridin-2-yl]piperazin-1-yl}sulfonyl)but-3-en-1-yl]pyrimidine (10.9 g, 23.7 mmol) in THF (200 mL) was added 50% aqueous solution of hydroxylamine (11 mL) and the reaction stirred at room temperature for 2 hours. Water (100 mL) was then added and then this was extracted with EtOAc (3×100 mL) and dried (brine, MgSO4), filtered and concentrated in vacuo to give 2-[3-(hydroxyamino)-4-({4-[5-(2,2,2-trifluoroethoxy)pyridin-2-yl]piperazin-1-yl}sulfonyl)butyl]pyrimidine as a pale yellow solid (11.1 g, 22.6 mmol, 96%).

Workup

  1. extractionthis was extracted with EtOAc (3×100 mL)
  2. dry with materialdried (brine, MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6cc08b7a7a3a4912945e9f06b81fd195
Source dataset
uspto-grants-2009_02
Patent number
US07485644B2

Reaction notes

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