Acetic Anhydride → HCID 57785927, compound

HRID 1628810Notes

Reaction equation

HRID 1628810 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[CH:20]=[CH:19][C:18]([C:21]([OH:24])([CH3:23])[CH3:22])=[CH:17][C:16]=4[Cl:25])[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([CH:26]([OH:29])[CH2:27][CH3:28])=[CH:4][CH:3]=1.[C:30](OC(=O)C)(=[O:32])[CH3:31]>N1C=CC=CC=1>[C:30]([O:29][CH:26]([C:5]1[C:6]2[N:7]3[CH2:14][CH2:13][CH2:12][N:11]([C:15]4[CH:20]=[CH:19][C:18]([C:21]([OH:24])([CH3:23])[CH3:22])=[CH:17][C:16]=4[Cl:25])[C:8]3=[N:9][C:10]=2[C:2]([Cl:1])=[CH:3][CH:4]=1)[CH2:27][CH3:28])(=[O:32])[CH3:31]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 57786171HCID 57786171, compound

Product 1

HCID 57785927HCID 57785927, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1-{9-chloro-1-[2-chloro-4-(1-hydroxy-1-methylethyl)phenyl]-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl}propan-1-ol (78.3 mg, 0.180 mmol) in pyridine (0.5 mL) was added acetic anhydride (0.2 mL) at 0° C. The reaction mixture was stirred at room temperature for 4 hrs. The mixture was concentrated. The residue was neutralized with aqueous saturated sodium hydrogen carbonate and extracted with ethyl acetate (×3). The combined organic layer was washed with brine (×1), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 0-40% ethyl acetate/n-hexane gradient mixture. The residue was recrystallized from ethanol/n-hexane to give the title compound as a colorless powder (47.4 mg, 0.0995 mmol, 55%).

Workup

  1. concentrationThe mixture was concentrated
  2. extractionextracted with ethyl acetate (×3)
  3. washThe combined organic layer was washed with brine (×1)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography
  8. washeluting with a 0-40% ethyl acetate/n-hexane gradient mixture
  9. customThe residue was recrystallized from ethanol/n-hexane

Sources & evidence

ORD record
ord-ce564cccf0074ea18f3a69fa7a6b8629
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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