Ammonium Chloride → HCID 178496765, compound

HRID 1059417Notes

Reaction equation

HRID 1059417 reaction equation
[CH3:1][Si:2]([CH:5]=[N+:6]=[N-:7])([CH3:4])[CH3:3].C([Li])CCC.C1(S([CH:22]=[CH:23][C:24]2[CH:25]=[CH:26][C:27]3[S:32][C:31]4[N:33]=[CH:34][CH:35]=[N:36][C:30]=4[N:29]([CH2:37][O:38][CH3:39])[C:28]=3[CH:40]=2)(=O)=O)C=CC=CC=1.[Cl-].[NH4+]>CCCCCC.O1CCCC1>[CH3:1][Si:2]([CH3:4])([CH3:3])[C:5]1[C:23]([C:24]2[CH:25]=[CH:26][C:27]3[S:32][C:31]4[N:33]=[CH:34][CH:35]=[N:36][C:30]=4[N:29]([CH2:37][O:38][CH3:39])[C:28]=3[CH:40]=2)=[CH:22][NH:7][N:6]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 167693TrimethylsilyldiazomethaneHCID 69884035HCID 69884035, compoundHCID 178418339Butyllithium

Product 1

HCID 178496765HCID 178496765, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

1.5 ml of a 2.0 M solution of (trimethylsilyl)-diazomethane in hexane was added to dry tetrahydrofuran (7 ml) in a nitrogen atmosphere and cooled to −78° C. After dropping 1.0 ml of a 1.6 M n-butyllithium solution in n-hexane thereinto, the resulting mixture was stirred for 30 minutes. Into the reaction mixture was dropped a solution of 410 mg of 8-(2-benzenesulfonylvinyl)-10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazine obtained in Example 1080-1 in dry tetrahydrofuran (5 ml). Then the reaction mixture was gradually heated to room temperature and an aqueous solution of ammonium chloride was added thereto followed by extraction with ethyl acetate. Then the mixture was dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography (eluted with ethyl acetate/n-hexane) to thereby give 130 mg of the title compound as yellow crystals.

Workup

  1. temperatureThen the reaction mixture was gradually heated to room temperature
  2. extractionthereto followed by extraction with ethyl acetate
  3. dry with materialThen the mixture was dried over anhydrous sodium sulfate
  4. distillationAfter distilling off the solvent under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (eluted with ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-789996e5ada24296a4b68a9242b091ec
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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