Diisopropylethylamine → HCID 67970905, compound

HRID 1184396Notes

Reaction equation

HRID 1184396 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10]([O:18][CH2:19][C:20]([F:23])([F:22])[F:21])=[N:11][CH:12]=[C:13]([CH:17]=2)[C:14](O)=[O:15])[CH:5]=[CH:6][C:7]=1[Cl:8].ClC(N(C)C)=C(C)C.C(N(CC)C(C)C)(C)C.[C:41]([O:45][C:46](=[O:49])[CH2:47][NH2:48])([CH3:44])([CH3:43])[CH3:42]>ClCCl>[C:41]([O:45][C:46](=[O:49])[CH2:47][NH:48][C:14]([C:13]1[CH:12]=[N:11][C:10]([O:18][CH2:19][C:20]([F:22])([F:23])[F:21])=[C:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH:17]=1)=[O:15])([CH3:44])([CH3:43])[CH3:42]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151417Glycine tert-butyl esterHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 67286406HCID 67286406, compound

Product 1

HCID 67970905HCID 67970905, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3.66 g 5-(3,4-dichloro-phenyl)-6-(2,2,2-trifluoro-ethoxy)-nicotinic acid in 40 ml dichloromethane was added 1.469 g Ghosez's reagent ((1-chloro-2-methyl-propenyl)-dimethyl-amine)) and the mixture was stirred at ambient temperature for 30 min. To the resulting solution was added 3.224 g N,N-diisopropylethylamine and 1.44 g glycine-t-butylester and the mixture was stirred at ambient temperature for 30 min. The reaction mixture was quenched by addition of 10% aqueous citric acid. The phases were separated and the organic phase was purified by chromatography on silica gel with heptane:ethyl acetate=9:1 to 1:1 to yield 4.10 g of the title compound as white foam. MS (EI): 477.0608 (M−H).

Workup

  1. stirringthe mixture was stirred at ambient temperature for 30 min
  2. customThe reaction mixture was quenched by addition of 10% aqueous citric acid
  3. customThe phases were separated
  4. customthe organic phase was purified by chromatography on silica gel with heptane

Sources & evidence

ORD record
ord-095e50101a374f318adb3cd66caf54dd
Source dataset
uspto-grants-2014_03
Patent number
US08669254B2

Reaction notes

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