Isopropylamine → HCID 21071279, compound

HRID 1371578Notes

Reaction equation

HRID 1371578 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].C[Al](C)C.[Br:9][C:10]1[CH:14]=[C:13]([C:15]([NH:17][C:18]2[CH:19]([C:25](OCC)=[O:26])[CH2:20][CH2:21][CH2:22][C:23]=2[CH3:24])=[O:16])[N:12]([C:30]2[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][N:31]=2)[N:11]=1>ClCCl>[Br:9][C:10]1[CH:14]=[C:13]([C:15]([NH:17][C:18]2[CH:23]([CH3:24])[CH2:22][CH2:21][CH2:20][C:19]=2[C:25]([NH:4][CH:1]([CH3:3])[CH3:2])=[O:26])=[O:16])[N:12]([C:30]2[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][N:31]=2)[N:11]=1

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 16682925TrimethylaluminumHCID 21071282HCID 21071282, compound2×

Product 1

HCID 21071279HCID 21071279, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Isopropyl amine (77 μL, 0.9 mmol) was added to a solution of trimethylaluminum (0.45 mL, 2M solution in hexanes, 0.9 mmol) in dichloromethane (10 mL). After stirring at ambient temperature for 1 h, ethyl 2-[[[3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]carbonyl]amino]-3-methyl-2-cyclohexene-1-carboxylate (i.e. the product of Step G) was added (425 mg, 0.9 mmol) in dichloromethane (5 mL) and the solution was heated at reflux for 24 hours and then overnight at ambient temperature. The reaction was quenched with water and the mixture was filtered through a column of celite and washed with dichloromethane. The eluent was concentrated and purified by silica gel column chromatography (eluted with 60% then 80% ethyl ether in petroleum ether then ethyl ether then ethyl acetate) to give the title compound, a compound of present invention, as a colorless oil (100 mg).

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 24 hours
  3. customovernight
  4. customat ambient temperature
  5. customThe reaction was quenched with water
  6. filtrationthe mixture was filtered through a column of celite
  7. washwashed with dichloromethane
  8. concentrationThe eluent was concentrated
  9. custompurified by silica gel column chromatography (
  10. washeluted with 60%

Sources & evidence

ORD record
ord-48549616935b4ce0b672768aa947dafe
Source dataset
uspto-grants-2007_01
Patent number
US07157475B2

Reaction notes

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