Triethylamine → HCID 59633401, compound

HRID 2369078Notes

Reaction equation

HRID 2369078 reaction equation
C(N(CC)CC)C.[CH3:8][N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N:22]1[C:26]([C:27]2[S:31][C:30]([S:32](Cl)(=[O:34])=[O:33])=[CH:29][CH:28]=2)=[CH:25][C:24]([C:36]([F:39])([F:38])[F:37])=[N:23]1>CN(C1C=CN=CC=1)C.ClCCCl>[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N:22]1[C:26]([C:27]2[S:31][C:30]([S:32]([N:12]3[CH2:13][CH2:14][N:9]([CH3:8])[CH2:10][CH2:11]3)(=[O:34])=[O:33])=[CH:29][CH:28]=2)=[CH:25][C:24]([C:36]([F:39])([F:37])[F:38])=[N:23]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 59631668HCID 59631668, compound

Product 1

HCID 59633401HCID 59633401, compoundYield 54.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolvent2×

Procedure

Triethylamine (0.15 mL, 1.1 mmol) and a small amount of DMAP were dissolved in 1,2-dichloroethane (2 mL) in a reaction vial. This solution was treated with 1-methyl piperazine (50 μL, 0.45 mmol) followed by 5-(1-(2-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)thiophene-2-sulfonyl chloride (145 mg, 0.34 mmol) as a solution in 1,2-dichloroethane (1 mL). After stirring 4½ hours at ambient temperature the reaction was quenched by dilution with CH2Cl2 and water. Saturated NaHCO3 was added and the basic aqueous was extracted with CH2Cl2 (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure to afford crude product as a pale yellow oil. This crude product was purified by flash column chromatography eluting with a gradient from CH2Cl2 to 16% acetonitrile/CH2Cl2 to afford 1-(5-(1-(2-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)thiophen-2-ylsulfonyl)-4-methylpiperazine (90.5 mg, 54% yield) as a brittle white foam. MS(ES): 491 [M+H]+.

Workup

  1. customwas quenched by dilution with CH2Cl2 and water
  2. additionSaturated NaHCO3 was added
  3. extractionthe basic aqueous was extracted with CH2Cl2 (3×)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto afford crude product as a pale yellow oil
  8. customThis crude product was purified by flash column chromatography
  9. washeluting with a gradient from CH2Cl2 to 16% acetonitrile/CH2Cl2

Sources & evidence

ORD record
ord-c81f194379934c20a764f568bc58a7bb
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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