Acetic Anhydride → HCID 10208941, compound

HRID 859931Notes

Reaction equation

HRID 859931 reaction equation
C(O[C:5](=[O:7])C)(=O)C.[OH:8][NH:9][CH:10]([CH2:35][CH2:36][CH2:37][C:38]1[N:43]=[CH:42][CH:41]=[CH:40][N:39]=1)[CH2:11][S:12]([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[N:26]=[CH:25][C:24]([C:27]#[C:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=3)=[CH:23][N:22]=2)[CH2:17][CH2:16]1)(=[O:14])=[O:13]>O1CCCC1.C(O)=O>[OH:8][N:9]([CH:10]([CH2:11][S:12]([N:15]1[CH2:16][CH2:17][N:18]([C:21]2[N:22]=[CH:23][C:24]([C:27]#[C:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=3)=[CH:25][N:26]=2)[CH2:19][CH2:20]1)(=[O:14])=[O:13])[CH2:35][CH2:36][CH2:37][C:38]1[N:39]=[CH:40][CH:41]=[CH:42][N:43]=1)[CH:5]=[O:7]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 86608428HCID 86608428, compound

Product 1

HCID 10208941HCID 10208941, compound

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

Formic acid (1.8 mL, 50 mmol) and acetic anhydride (0.5 mL, 5 mmol) were mixed together at 0° C. for 30 minutes, before being added to a solution 2-(4-{[2-(hydroxyamino)-5-pyrimidin-2-ylpentyl]sulfonyl}piperazin-1-yl)-5-(pyridin-2-ylethynyl)pyrimidine (190 mg, 0.37 mmol) in tetrahydrofuran (5 mL) and formic acid (1.8 mL) at 0° C. The reaction was allowed to reach room temperature and was stirred for 45 minutes. The reaction was then evaporated in vacuo, and azeotroped with toluene (2×5 mL). The residue was then dissolved in MeOH and heated to 45° C. for one hour. The solution was evaporated in vacuo, and the residue triturated with Et2O to give a white solid which was collected by filtration, washed with Et2O and dried in vacuo to give hydroxy {1-[({4-[5-(pyridin-2-ylethynyl)pyrimidin-2-yl]piperazin 1-yl}sulfonyl)methyl]-4-pyrimidin-2-ylbutyl}formamide as a white solid. (64 mg, 32%).

Workup

  1. customto reach room temperature
  2. customThe reaction was then evaporated in vacuo
  3. customazeotroped with toluene (2×5 mL)
  4. dissolutionThe residue was then dissolved in MeOH
  5. customThe solution was evaporated in vacuo
  6. customthe residue triturated with Et2O
  7. customto give a white solid which
  8. filtrationwas collected by filtration
  9. washwashed with Et2O
  10. customdried in vacuo

Sources & evidence

ORD record
ord-276cdd3bd7324cda8c4092cc712aa606
Source dataset
uspto-grants-2006_12
Patent number
US07153857B2

Reaction notes

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