Pyridine → HCID 67280567, compound

HRID 1693310Notes

Reaction equation

HRID 1693310 reaction equation
[NH2:1][CH2:2][C:3]1[C:12]2[CH2:11][S:10][N:9]=[C:8]([N:13](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)[C:7]3=[N:28][N:29]([CH2:31][C:32]4[C:37]([CH3:38])=[C:36]([O:39][CH3:40])[C:35]([CH3:41])=[CH:34][N:33]=4)[N:30]=[C:5]([C:6]=23)[CH:4]=1.N1C=CC=CC=1.[C:48](OC(=O)C)(=[O:50])[CH3:49]>ClCCl>[NH2:13][C:8]1[C:7]2[C:6]3[C:5](=[N:30][N:29]([CH2:31][C:32]4[C:37]([CH3:38])=[C:36]([O:39][CH3:40])[C:35]([CH3:41])=[CH:34][N:33]=4)[N:28]=2)[CH:4]=[C:3]([CH2:2][NH:1][C:48](=[O:50])[CH3:49])[C:12]=3[CH2:11][S:10][N:9]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 86641345HCID 86641345, compound

Product 1

HCID 67280567HCID 67280567, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture composed of di-tert-butyl {8-(aminomethyl)-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-2,7-dihydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-4-yl}imidodicarbonate of Example 112 (20 mg), pyridine (8.3 μl), acetic anhydride (5 μl) and dichloromethane (0.5 ml) was stirred at room temperature for 20 hours. The reaction mixture was concentrated under reduced pressure. Dichloromethane (2 ml) and trifluoroacetic acid (0.5 ml) were added to the resulting residue, and the mixture was stirred at room temperature for 20 hours. The reaction mixture was concentrated under reduced pressure. A saturated sodium bicarbonate solution was placed into the resulting residue, followed by extraction with chloroform. The organic layer was dried over sodium sulfate and filtered. Then, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel thin-layer chromatography (chloroform-methanol) to obtain the title compound (3.7 mg) as a solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionDichloromethane (2 ml) and trifluoroacetic acid (0.5 ml) were added to the resulting residue
  3. stirringthe mixture was stirred at room temperature for 20 hours
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. extractionfollowed by extraction with chloroform
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationThen, the filtrate was concentrated under reduced pressure
  9. customThe resulting residue was purified by silica gel thin-layer chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-5dd27f48b1e3450bb68d9cdbfb8acbf4
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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