Tetrahydrofuran → HCID 10187195, compound

HRID 859927Notes

Reaction equation

HRID 859927 reaction equation
[OH:1][NH:2][CH:3]([CH2:13][S:14]([N:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:28]=[CH:27][C:26]([C:29]#[C:30][C:31]3[S:32][CH:33]=[CH:34][CH:35]=3)=[CH:25][N:24]=2)[CH2:19][CH2:18]1)(=[O:16])=[O:15])[CH2:4][CH2:5][CH2:6][C:7]1[N:12]=[CH:11][CH:10]=[CH:9][N:8]=1.C1C[O:39][CH2:38]C1>>[OH:1][N:2]([CH:3]([CH2:13][S:14]([N:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:28]=[CH:27][C:26]([C:29]#[C:30][C:31]3[S:32][CH:33]=[CH:34][CH:35]=3)=[CH:25][N:24]=2)[CH2:19][CH2:18]1)(=[O:16])=[O:15])[CH2:4][CH2:5][CH2:6][C:7]1[N:12]=[CH:11][CH:10]=[CH:9][N:8]=1)[CH:38]=[O:39]

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 86594847HCID 86594847, compound

Product 1

HCID 10187195HCID 10187195, compoundYield 54%

Conditions

Temperature
40 °C

Procedure

and a solution of 2-[4-(hydroxyamino)-5-({4-[5-(thien-2-ylethynyl)pyridin-2-yl]piperazin-1-yl}sulfonyl)pentyl]pyrimidine (84 mg, 0.16 mmol) in THF (8 mL) was then added. The reaction was brought to RT and stirred for one hour. Volatiles were then removed in vacuo, and the residue azeotroped with toluene (2×5 mL). The residue was then dissolved in MeOH (10 mL) and heated to 40° C. for one hour. The solution was then cooled to RT and concentrated in vacuo. The residue was then purified by flash chromatography (silica gel, 10% MeOH in EtOAc) to give the title compound as an off-white foam (87 mg, 0.16 mmol, 54%).

Workup

  1. customwas brought to RT
  2. customVolatiles were then removed in vacuo
  3. customthe residue azeotroped with toluene (2×5 mL)
  4. dissolutionThe residue was then dissolved in MeOH (10 mL)
  5. temperatureThe solution was then cooled to RT
  6. concentrationconcentrated in vacuo
  7. customThe residue was then purified by flash chromatography (silica gel, 10% MeOH in EtOAc)

Sources & evidence

ORD record
ord-8603a902811448c095eb14e697ed8f2e
Source dataset
uspto-grants-2006_12
Patent number
US07153857B2

Reaction notes

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