Diisopropylamine → HCID 19852318, compound

HRID 978165Notes

Reaction equation

HRID 978165 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 a method analogous to that described above 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 solidifed 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-dafa32338e3f4318ae949c391047abc3
Source dataset
uspto-grants-1987_05
Patent number
US04663341

Reaction notes

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