Triethylamine → HCID 22293795, compound

HRID 967369Notes

Reaction equation

HRID 967369 reaction equation
FC(F)(F)C([O-])=O.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:19]3[CH2:20][NH:21][CH2:22][CH2:23][C:18]=3[NH2+:17][N:16]=2)=[CH:11][CH:10]=1.CCN(CC)CC.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>CN(C=O)C>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[C:19]3[CH2:20][N:21]([S:32]([CH3:31])(=[O:34])=[O:33])[CH2:22][CH2:23][C:18]=3[NH:17][N:16]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22293620HCID 22293620, compound

Product 1

HCID 22293795HCID 22293795, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3.11 g (11.1 mmol) of 3-(4-bromophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridinium trifluoroacetate and 4.71 mL (33.5 mmol) of Et3N in DMF (55 mL) was slowly added 1.21 mL (15.6 mmol) of methanesulfonyl chloride. After 2.5 h, the solvent was removed under reduced pressure and the residue was diluted with CH2Cl2 (100 mL) and saturated NaHCO3 (100 mL). The layers were separated and the aqueous phase was extracted with CH2Cl2 (2×30 mL). The combined organic layers were dried over Na2SO4 and the solvent was removed under reduced pressure. Purification by column chromatography (silica, 0-5% MeOH/CH2Cl2) afforded 2.01 g (50%) of the title compound. TLC (silica, 5% MeOH/CH2Cl2): Rf=0.3. MS (electrospray): m/z calculated for C13H14BrN3O2S [M++H] 356.00, observed 356.0.

Workup

  1. customthe solvent was removed under reduced pressure
  2. additionthe residue was diluted with CH2Cl2 (100 mL) and saturated NaHCO3 (100 mL)
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with CH2Cl2 (2×30 mL)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. customthe solvent was removed under reduced pressure
  7. customPurification by column chromatography (silica, 0-5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-57d9e31ed68948d9aaff03f266be365c
Source dataset
uspto-grants-2005_10
Patent number
US06953793B2

Reaction notes

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