Diisopropylethylamine → HCID 18387376, compound

HRID 369747

Reaction equation

HRID 369747 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:16]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)=[CH:17][CH:18]=1)[C:5]([OH:15])([C:10]#[C:11][CH:12]1[CH2:14][CH2:13]1)[C:6]([F:9])([F:8])[F:7].C(N(C(C)C)CC)(C)C.Br[CH:39]([CH2:43][CH2:44][Br:45])[C:40](Cl)=[O:41]>C(Cl)Cl>[Br:45][CH2:44][CH2:43][CH:39]1[O:15][C:5]([C:10]#[C:11][CH:12]2[CH2:13][CH2:14]2)([C:6]([F:7])([F:8])[F:9])[C:4]2[CH:3]=[C:2]([Cl:1])[CH:18]=[CH:17][C:16]=2[N:19]([CH2:20][C:21]2[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=2)[C:40]1=[O:41]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 44131432,4-Dibromobutyryl chlorideHCID 206854532-(5-Chloro-2-{[(4-methoxyphenyl)methyl]amino}phenyl)-4-cyclopropyl-1,1,1-trifluorobut-3-yn-2-ol

Product 1

HCID 18387376HCID 18387376, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.64 g of 3-chloro-6-(4-methoxyphenyl)methylamino-α-cyclopropylethynyl-α-(trifluoromethyl)benzyl alcohol and 2.0 mL of diisopropylethylamine in 30 mL of dry methylene chloride was added 1.6 g of 2,4-dibromobutyryl chloride. After stirring at room temperature overnight, the mixture was poured onto water and extracted with ether. The ether layer was washed with aqueous sodium bicarbonate, dried, and evaporated to an oil. This material was subjected to column chromatography over silica gel (elution with 5-10% ethyl acetate in hexanes) affording 1.13 g of the title compound as a mixture of diastereomers.

Workup

  1. additionthe mixture was poured onto water
  2. extractionextracted with ether
  3. washThe ether layer was washed with aqueous sodium bicarbonate
  4. customdried
  5. customevaporated to an oil

Sources & evidence

ORD record
ord-b1ca2c5d38364f96952f6c10d23e85e5
Source dataset
uspto-grants-2000_10
Patent number
US06140320

Linked notes

Loading…