Diisopropylamine → HCID 19852318, compound

HRID 1607218Notes

Reaction equation

HRID 1607218 reaction equation
C(NC(C)C)(C)C.[CH2:8]([Li])[CH2:9][CH2:10][CH3:11].[Br:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]([N:23]2[CH2:27][CH:26]([CH3:28])[C:25]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)=[N:24]2)=[O:22])=[CH:16][CH:15]=1.CCC(C1C=CC(F)=CC=1)=O.BrC1C=CC(N=C=O)=CC=1.ICCCC>O1CCCC1.CCCCCC.C(O)(=O)C>[Br:13][C:14]1[CH:15]=[CH:16][C:17]([NH:20][C:21]([N:23]2[CH2:27][C:26]([CH2:8][CH2:9][CH2:10][CH3:11])([CH3:28])[C:25]([C:29]3[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=3)=[N:24]2)=[O:22])=[CH:18][CH:19]=1

Participants

10

Reactant 6

HCID 7912DiisopropylamineHCID 10962Butyl iodideHCID 680044-FluoropropiophenoneHCID 756094-Bromophenyl isocyanateHCID 19852359HCID 19852359, compoundHCID 178418339Butyllithium

Product 1

HCID 19852318HCID 19852318, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To 2.1 g of diisopropylamine dissolved in 15 ml of tetrahydrofuran and cooled in an ice salt bath was added 8.0 ml of a 2.7 molar solution of n-butyllithium in hexane. After stirring for 5 minutes a solution of 3.7 g of N-(4-bromophenyl)-3-(4-fluorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide (prepared from 4-fluoropropiophenone and 4-bromophenyl isocyanate by substantially following the procedures described in Examples E, F, and G) in 15 ml of tetrahydrofuran was added and the resulting solution stirred for 15 minutes. To this solution was added 1.5 ml of 1-iodobutane and, after 15 minutes 1.5 ml of acetic acid was added. The reaction mixture was partitioned between diethyl ether and water and the organic layer was dried over anhydrous magnesium sulfate. The resulting solution was filtered, evaporated in vacuo, and chromatographed to give 2.9 g of N-(4-bromophenyl)-3-(4-fluorophenyl)-4-butyl-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide an oil that solidified on long standing. NMR and IR data were consistent with the structure.

Workup

  1. temperaturecooled in an ice salt bath
  2. additionwas added
  3. customThe reaction mixture was partitioned between diethyl ether and water
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationThe resulting solution was filtered
  6. customevaporated in vacuo
  7. customchromatographed

Sources & evidence

ORD record
ord-cc0c1f2a874e43b681a56d8e7c563f15
Source dataset
uspto-grants-1989_09
Patent number
US04863947

Reaction notes

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