Acetic Acid → HCID 58465582, compound

HRID 1255456Notes

Reaction equation

HRID 1255456 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]2[N:6]3[C:10]([CH2:11][NH:12][CH2:13][C:4]=2[CH:3]=1)=[N:9][N:8]=[C:7]3[CH:14]1[CH2:19][CH2:18][C:17]([C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][N:21]=2)=[CH:16][CH2:15]1.[C:29](O)(=O)C.C=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]2[N:6]3[C:10]([CH2:11][N:12]([CH3:29])[CH2:13][C:4]=2[CH:3]=1)=[N:9][N:8]=[C:7]3[CH:14]1[CH2:19][CH2:18][C:17]([C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][N:21]=2)=[CH:16][CH2:15]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 58465561HCID 58465561, compound

Product 1

HCID 58465582HCID 58465582, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of (RS)-8-chloro-1-[4-(4-fluoro-pyridin-2-yl)-cyclohex-3-enyl]-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulene (0.032 g, 0.081 mmol), acetic acid (0.028 ml, 0.49 mmol) and paraformaldehyde (0.010 g, 0.32 mmol) in 1,2-dichloroethane (0.8 ml) was stirred for 16 h at room temperature. Addition of sodium triacetoxyborohydride (0.103 g, 0.49 mmol) was followed by stirring at room temperature for further 3 h. The mixture was partitioned between dichloromethane (50 ml) and 0.5 M aqueous sodium hydroxide solution (50 ml). The layers were separated. The aqueous layer was extracted with one 50 ml-portion of dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. Flash chromatography with n-heptane/isopropanol as eluent gave the title compound (0.026 g, 79%) as white solid. MS m/e: 410 ([M+H]+)

Workup

  1. stirringby stirring at room temperature for further 3 h
  2. customThe mixture was partitioned between dichloromethane (50 ml) and 0.5 M aqueous sodium hydroxide solution (50 ml)
  3. customThe layers were separated
  4. extractionThe aqueous layer was extracted with one 50 ml-portion of dichloromethane
  5. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-26121ebfe1864a8589ce049a3cb928b5
Source dataset
uspto-grants-2013_06
Patent number
US08461151B2

Reaction notes

Loading…