Formic Acid → HCID 10282266, compound

HRID 859916Notes

Reaction equation

HRID 859916 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][C:44]([C:47]([F:50])([F:49])[F:48])=[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[CH2:28][CH2:29][N:30]([C:33]2[CH:38]=[CH:37][C:36]([C:39]#[C:40][C:41]3[CH:46]=[CH:45][C:44]([C:47]([F:50])([F:49])[F:48])=[CH:43][N:42]=3)=[CH:35][N:34]=2)[CH2:31][CH2:32]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 Acid2×HCID 7918Acetic AnhydrideHCID 86608427HCID 86608427, compound

Product 1

HCID 10282266HCID 10282266, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To formic acid (0.36 mL, 9.5 mmol) at 0° C. was added acetic anhydride (90 μL, 0.95 mmol) and the mixture was stirred at RT for 10 minutes. The reaction was then recooled to 0° C., and added to a solution of 2-(4-(hydroxyamino)-5-{[4-(5-{[5-(trifluoromethyl)pyridin-2-yl]ethynyl}pyridin-2-yl)piperazin-1-yl]sulfonyl}pentyl)pyrimidine (403 mg, 0.79 mmol) and formic acid (0.36 mL, 9.5 mmol) in THF (3 mL) at 0° C. 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 (66 mg, 0.11 mmol, 58%).

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-3cbf69bbdd9340158aecad6eacd4258d
Source dataset
uspto-grants-2006_12
Patent number
US07153857B2

Reaction notes

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