Triethylamine → HCID 178426031, compound

HRID 536756Notes

Reaction equation

HRID 536756 reaction equation
[C:1]([C:5]1[N:9]([CH3:10])[N:8]([CH2:11][CH:12]2[CH2:15][CH2:14][CH2:13]2)[C:7](=[NH:16])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[F:24][C:25]1[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][C:26]=1[C:27](Cl)=[O:28]>C1COCC1>[C:1]([C:5]1[N:9]([CH3:10])[N:8]([CH2:11][CH:12]2[CH2:13][CH2:14][CH2:15]2)/[C:7](=[N:16]/[C:27](=[O:28])[C:26]2[CH:30]=[C:31]([CH3:34])[CH:32]=[CH:33][C:25]=2[F:24])/[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70180482-Fluoro-5-methylbenzoyl chlorideHCID 666432695-Tert-butyl-2-(cyclobutylmethyl)-1-methyl-1h-pyrazol-3(2h)-imine

Product 1

HCID 178426031HCID 178426031, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 113C (0.30 g, 1.4 mmol) and Et3N (0.56 mL, 4.1 mmol) in THF (10 mL) was added 2-fluoro-5-methylbenzoyl chloride (0.23 g, 1.4 mmol). The mixture was stirred at ambient temperature for 4 hours then partitioned between saturated aqueous NaHCO3 (10 mL) and EtOAc (10 mL). The layers were separated and the aqueous phase was extracted EtOAc (3×10 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure. Purification by column chromatography (SiO2, 50% hexanes in EtOAc to 100% EtOAc to 9:1:0.1 EtOAc:MeOH:Et3N) afforded the title compound (0.24 g, 0.67 mmol, 50% yield). MS (ESI+) m/z 358 (M+H)+.

Workup

  1. customthen partitioned between saturated aqueous NaHCO3 (10 mL) and EtOAc (10 mL)
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted EtOAc (3×10 mL)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by column chromatography (SiO2, 50% hexanes in EtOAc to 100% EtOAc to 9:1:0.1 EtOAc:MeOH:Et3N)

Sources & evidence

ORD record
ord-71549a18cd7749f49abd95e1287d319b
Source dataset
uspto-grants-2014_10
Patent number
US08859596B2

Reaction notes

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