Acetic Anhydride → HCID 57531447, compound

HRID 1455754Notes

Reaction equation

HRID 1455754 reaction equation
[NH2:1][CH2:2][C:3]1[C:8]([CH2:9][N:10]([CH3:21])[C@@H:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][CH2:13][CH2:12]2)=[C:7]([CH3:22])[N:6]=[C:5]([C:23]2[C:28]([CH2:29][CH3:30])=[CH:27][CH:26]=[CH:25][C:24]=2[CH2:31][CH3:32])[N:4]=1.[C:33](OC(=O)C)(=[O:35])[CH3:34]>C(Cl)(Cl)Cl>[CH2:29]([C:28]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:31][CH3:32])[C:23]=1[C:5]1[N:4]=[C:3]([CH2:2][NH:1][C:33](=[O:35])[CH3:34])[C:8]([CH2:9][N:10]([CH3:21])[C@@H:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][CH2:13][CH2:12]2)=[C:7]([CH3:22])[N:6]=1)[CH3:30]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 57531599HCID 57531599, compound

Product 1

HCID 57531447HCID 57531447, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a vial containing (1S)-N-{[4-(aminomethyl)-2-(2,6-diethylphenyl)-6-methylpyrimidin-5-yl]methyl}-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine (9 mg, 0.021 mmol) in CHCl3 (2.0 mL) is added acetic anhydride (0.05 mL, 25.0 eq., 0.53 mmol) and allowed to stir at room temperature for 2 h. All solvent is then removed and excess acetic anhydride is removed azeotropically with toluene (3×2 mL). The sample is re-dissolved in CHCl3 and eluted through a plug of SiO2, washing with CHCl3. Concentration affords the title compound as a colorless gum. [mass expected (470.65); mass found (470.34)].

Workup

  1. customAll solvent is then removed
  2. customexcess acetic anhydride is removed azeotropically with toluene (3×2 mL)
  3. dissolutionThe sample is re-dissolved in CHCl3
  4. washeluted through a plug of SiO2
  5. washwashing with CHCl3
  6. concentrationConcentration

Sources & evidence

ORD record
ord-db07e66829b74e9e912f73dab58a2b21
Source dataset
uspto-grants-2009_01
Patent number
US07482350B2

Reaction notes

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