Hydroxylamine → HCID 87909955, compound

HRID 859930Notes

Reaction equation

HRID 859930 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH:11]=[CH:12][C:13]([N:16]3[CH2:21][CH2:20][N:19]([S:22]([CH:25]=[CH:26][CH2:27][CH2:28][CH2:29][C:30]4[N:35]=[CH:34][CH:33]=[CH:32][N:31]=4)(=[O:24])=[O:23])[CH2:18][CH2:17]3)=[N:14][CH:15]=2)=[CH:4][CH:3]=1.[NH2:36][OH:37]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH:11]=[CH:12][C:13]([N:16]3[CH2:17][CH2:18][N:19]([S:22]([CH2:25][CH:26]([NH:36][OH:37])[CH2:27][CH2:28][CH2:29][C:30]4[N:35]=[CH:34][CH:33]=[CH:32][N:31]=4)(=[O:24])=[O:23])[CH2:20][CH2:21]3)=[N:14][CH:15]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 69606773HCID 69606773, compound

Product 1

HCID 87909955HCID 87909955, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{(4EZ)-5-[(4-{5-[(4-fluorophenyl)ethynyl]pyridin-2-yl}piperazin-1-yl)sulfonyl]pent-4-enyl}pyrimidine (760 mg, 1.55 mmol) in THF (10 mL) was added a solution of hydroxylamine (2 mL, 50% aqueous solution in water). The reaction was stirred for 2 hours at RT before being quenched with saturated aqueous ammonium chloride solution (5 mL). The layers were separated and the aqueous phase extracted with ethyl acetate (3×20 mL). The combined organic extracts were then dried, (MgSO4), filtered and concentrated in vacuo. The residue was then purified by bond elut (silica, EtOAc to 10% MeOH in ethyl acetate) to give 2-[5-[(4-{5-[(4-fluorophenyl)ethynyl]pyridin-2-yl}piperazin-1-yl)sulfonyl]-4-(hydroxyamino)pentyl]pyrimidine (518 mg, 0.99 mmol, 64%).

Workup

  1. custombefore being quenched with saturated aqueous ammonium chloride solution (5 mL)
  2. customThe layers were separated
  3. extractionthe aqueous phase extracted with ethyl acetate (3×20 mL)
  4. dry with materialThe combined organic extracts were then dried, (MgSO4),
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was then purified by bond elut (silica, EtOAc to 10% MeOH in ethyl acetate)

Sources & evidence

ORD record
ord-bca8ea4e71dd480e8dc52078a27329ba
Source dataset
uspto-grants-2006_12
Patent number
US07153857B2

Reaction notes

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