Formic Acid → HCID 9915111, compound

HRID 859912Notes

Reaction equation

HRID 859912 reaction equation
[CH:1]([OH:3])=O.C(OC(=O)C)(=O)C.[OH:11][NH:12][CH:13]([CH2:23][S:24]([N:27]1[CH2:32][CH2:31][N:30]([C:33]2[CH:38]=[CH:37][C:36]([C:39]#[C:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=3)=[CH:35][N:34]=2)[CH2:29][CH2:28]1)(=[O:26])=[O:25])[CH2:14][CH2:15][CH2:16][C:17]1[N:22]=[CH:21][CH:20]=[CH:19][N:18]=1>C1COCC1>[OH:11][N:12]([CH:13]([CH2:23][S:24]([N:27]1[CH2:32][CH2:31][N:30]([C:33]2[CH:38]=[CH:37][C:36]([C:39]#[C:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=3)=[CH:35][N:34]=2)[CH2:29][CH2:28]1)(=[O:26])=[O:25])[CH2:14][CH2:15][CH2:16][C:17]1[N:18]=[CH:19][CH:20]=[CH:21][N:22]=1)[CH:1]=[O:3]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 86594843HCID 86594843, compound

Product 1

HCID 9915111HCID 9915111, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To formic acid (1.5 mL, 39 mmol) at 0° C. was added acetic anhydride (375 μL, 3.9 mmol) and the mixture was stirred at RT for 10 minutes. The reaction was then recooled to 0° C., and a solution of 2-[4-(hydroxyamino)-5-({4-[5-(pyridin-2-ylethynyl)pyridin-2-yl]piperazin-1-yl}sulfonyl)pentyl]pyrimidine (403 mg, 0.79 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 a pale yellow foam (231 mg, 0.43 mmol, 54%).

Workup

  1. customwas then recooled to 0° C.
  2. customwas brought to RT
  3. stirringstirred for one hour
  4. customVolatiles were then removed in vacuo
  5. customthe residue azeotroped with toluene (2×5 mL)
  6. dissolutionThe residue was then dissolved in MeOH (10 mL)
  7. temperatureheated to 40° C. for one hour
  8. temperatureThe solution was then cooled to RT
  9. concentrationconcentrated in vacuo
  10. customThe residue was then purified by flash chromatography (silica gel, 10% MeOH in EtOAc)

Sources & evidence

ORD record
ord-d7b45fcb6b984af4a938ecc5ec59f493
Source dataset
uspto-grants-2006_12
Patent number
US07153857B2

Reaction notes

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