Triethylamine → N-(1-tert-butyl-3-(3-methoxyphenethyl)-1H-pyrazol-5-yl)-4-(4-(methylsulfonyl)piperazin-1-yl)benzamide

HRID 16787Notes

Reaction equation

HRID 16787 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([N:10]1[C:14]([NH:15][C:16](=[O:29])[C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)=[CH:19][CH:18]=2)=[CH:13][C:12]([CH2:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[CH:33]=2)=[N:11]1)([CH3:9])([CH3:8])[CH3:7].C(N(CC)CC)C>C(Cl)Cl.C(=O)([O-])O.[Na+]>[C:6]([N:10]1[C:14]([NH:15][C:16](=[O:29])[C:17]2[CH:18]=[CH:19][C:20]([N:23]3[CH2:28][CH2:27][N:26]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:25][CH2:24]3)=[CH:21][CH:22]=2)=[CH:13][C:12]([CH2:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[CH:33]=2)=[N:11]1)([CH3:9])([CH3:8])[CH3:7]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66589920N-(1-tert-butyl-3-(3-methoxyphenethyl)-1H-pyrazol-5-yl)-4-(piperazin-1-yl)benzamide

Product 1

HCID 66589934N-(1-tert-butyl-3-(3-methoxyphenethyl)-1H-pyrazol-5-yl)-4-(4-(methylsulfonyl)piperazin-1-yl)benzamideYield 94.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
20 °C

Procedure

Methanesulphonyl chloride (0.042 mL, 0.55 mmol) was added at 0° C. to a solution of N-(1-tert-butyl-3-(3-methoxyphenethyl)-1H-pyrazol-5-yl)-4-(piperazin-1-yl)benzamide (0.231 g, 0.5 mmol) and N,N-diethylethanamine (0.077 mL, 0.55 mmol) in DCM (4 mL). The resulting solution was stirred at 20° C. for 1 h. The reaction mixture was diluted with saturated sodium hydrogen carbonate (10 ml) filtered and the solid washed with DCM (2×10 ml). The organic layers were combined and washed with water (20 ml) and saturated brine (20 ml). The organics were dried (MgSO4), filtered and evaporated to afford crude product. The crude product was purified by silica column chromatography, eluting with a gradient of 0-5% MeOH in DCM. Pure fractions were evaporated to dryness to afford N-(1-tert-butyl-3-(3-methoxyphenethyl)-1H-pyrazol-5-yl)-4-(4-(methylsulfonyl)piperazin-1-yl)benzamide (0.255 g, 94%) as a white solid. MS: m/z=540 (MH+).

Workup

  1. filtrationfiltered
  2. washthe solid washed with DCM (2×10 ml)
  3. washwashed with water (20 ml) and saturated brine (20 ml)
  4. dry with materialThe organics were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto afford crude product
  8. customThe crude product was purified by silica column chromatography
  9. washeluting with a gradient of 0-5% MeOH in DCM
  10. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-6f70dd3271a04f17b0da5b153861d780
Source dataset
uspto-grants-2010_06
Patent number
US07737149B2

Reaction notes

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