Formaldehyde → (S)-10-[3-(4-methoxybutyl)-4-methyl-piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene

HRID 131468Notes

Reaction equation

HRID 131468 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[NH:12][CH2:11][CH2:10][N:9]([C:13]2[C:22]3[CH:21]=[C:20]([CH3:23])[S:19][C:18]=3[NH:17][C:16]3[CH:24]=[CH:25][CH:26]=[CH:27][C:15]=3[N:14]=2)[CH2:8]1.[CH2:28]=O>ClC(Cl)C.O.[OH-].[Na+]>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[N:12]([CH3:28])[CH2:11][CH2:10][N:9]([C:13]2[C:22]3[CH:21]=[C:20]([CH3:23])[S:19][C:18]=3[NH:17][C:16]3[CH:24]=[CH:25][CH:26]=[CH:27][C:15]=3[N:14]=2)[CH2:8]1

Participants

6

Reactant 2

HCID 712FormaldehydeHCID 135430626(S)-10-[3-(4-methoxybutyl)-piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene

Product 1

HCID 136090333(S)-10-[3-(4-methoxybutyl)-4-methyl-piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 63651,1-DichloroethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

Into a room temperature, stirred solution of (S)-10-[3-(4-methoxybutyl)-piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene (0.031 g, 0.08 mmol), and formaldehyde solution (0.082 mL, 0.10 mmol, 37% in H2O) in dichloroethane (0.5 mL) was added NaHB(OAc)3 (0.026 g, 0.12 mmol) and stirred overnight. Dilute the solution with H2O (20 mL), 1.0 N NaOH (1 mL) and extract with CH2Cl2 (3×40 mL). Dry the combined organic layers over Na2SO4, and filter. Concentrate the mixture under reduced pressure and purify by silica gel chromatography eluting with 10% (33% 2 M NH3 in MeOH/64% EtOH)/CH2Cl2. Combine the purified fractions, concentrate under reduced pressure, and place under vacuum to give the title compound: orange solid (0.014 g), mass spectrum (m/e):399.3 (M+H).

Workup

  1. extractionextract with CH2Cl2 (3×40 mL)
  2. dry with materialDry the combined organic layers over Na2SO4
  3. filtrationfilter
  4. concentrationConcentrate the mixture under reduced pressure
  5. custompurify by silica gel chromatography
  6. washeluting with 10% (33% 2 M NH3 in MeOH/64% EtOH)/CH2Cl2
  7. concentrationconcentrate under reduced pressure, and place under vacuum

Sources & evidence

ORD record
ord-685da8c57eb54f25a03d34c52da27110
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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