4-tert-Butylbenzoyl chloride → HCID 86652265, compound

HRID 1409124Notes

Reaction equation

HRID 1409124 reaction equation
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9](Cl)=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])(O)=O.[Na+].[Cl:19][C:20]1[N:25]2[N:26]=[C:27]([CH3:29])[CH:28]=[C:24]2[N:23]=[C:22]([NH2:30])[C:21]=1[CH3:31]>>[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH:30][C:22]2[C:21]([CH3:31])=[C:20]([Cl:19])[N:25]3[N:26]=[C:27]([CH3:29])[CH:28]=[C:24]3[N:23]=2)=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:19][C:20]1[N:25]2[N:26]=[C:27]([CH3:29])[CH:28]=[C:24]2[N:23]=[C:22]([NH:30][C:9](=[O:10])[CH3:8])[C:21]=1[CH3:31]

Participants

5

Reactant 3

HCID 743724-tert-Butylbenzoyl chlorideHCID 516892Sodium BicarbonateHCID 58206890HCID 58206890, compound2×

Product 2

HCID 86652265HCID 86652265, compoundYield 31%HCID 86652266HCID 86652266, compoundYield 9%

Conditions

Temperature
100 °C

Procedure

7-Chloro-2,6-dimethylpyrazolo[1,5-a]pyrimidin-5-amine (5E, 1.0 equivalent) and 4-t-butylbenzoic acid chloride (2.0 equivalents) were dissolved in DMA (0.5 M with respect to 5E) and were heated to 100° C. for 18 h. After cooling to room temperature, saturated NaHCO3 was added and the mixture was extracted with EtOAc. Combined organic layers were dried over MgSO4, filtered and concentrated. The crude product was purified by chromatography (SiO2) to give 4-tert-butyl-N-(7-chloro-2,6-dimethylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide (5F, 31%) and N-(7-chloro-2,6-dimethylpyrazolo[1,5-a]pyrimidin-5-yl)acetamide (5G, 9%) as white solids.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted with EtOAc
  3. dry with materialCombined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by chromatography (SiO2)

Sources & evidence

ORD record
ord-dd933760e1414a8496d6bdeaae2faf54
Source dataset
uspto-grants-2014_12
Patent number
US08921358B2

Reaction notes

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