Vinyl Acetate → HCID 57786147, compound

HRID 1399174Notes

Reaction equation

HRID 1399174 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[Cl:7][C:8]1[C:16]2[N:15]=[C:14]3[N:17]([C:21]4[C:22]([CH3:29])=[N:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=4)[CH2:18][CH2:19][CH2:20][N:13]3[C:12]=2[C:11]([CH:30]([OH:33])[CH2:31][CH3:32])=[CH:10][CH:9]=1.[C:34](OC=C)(=O)[CH3:35]>C1C(Cl)=CC=C(Cl)C=1>[Cl:7][C:8]1[C:16]2[N:15]=[C:14]3[N:17]([C:21]4[C:22]([CH3:29])=[N:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=4)[CH2:18][CH2:19][CH2:20][N:13]3[C:12]=2[C:11]([CH:30]([O:33][CH:34]=[CH2:35])[CH2:31][CH3:32])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 7904Vinyl AcetateHCID 10340Sodium CarbonateHCID 57786288HCID 57786288, compound

Product 1

HCID 57786147HCID 57786147, compound

Reagents, catalysts & solvents 1

HCID 46851,4-DichlorobenzeneSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of sodium carbonate (16.4 mg, 0.155 mmol) in dichlorobenzene (0.5 mL) were added di-μ-chlorobis[(η-cycloocta-1,5-diene)iridium(I)] (8.7 mg, 0.0129 mmol), 1-[9-chloro-1-(6-methoxy-2-methylpyridin-3-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]propan-1-ol (100.0 mg, 0.155 mmol) and vinyl acetate (47.7 μL, 0.517 mmol). The reaction mixture was stirred at 100° C. for 3.5 hrs. The mixture was concentrated. The residue was purified by silica gel column chromatography eluting with a 0-40% ethyl acetate/n-hexane gradient mixture to give the title compound as a colorless amorphous (66.4 mg, 0.161 mmol, 62%).

Workup

  1. concentrationThe mixture was concentrated
  2. customThe residue was purified by silica gel column chromatography
  3. washeluting with a 0-40% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-abda1b66989f48eea748a3c615c03c6d
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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