Diisopropylethylamine → HCID 178483655, compound

HRID 2118245Notes

Reaction equation

HRID 2118245 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]([OH:13])=[O:12])[CH2:7][CH2:6]1.Cl.CCN(C(C)C)C(C)C.Cl[C:25]1[N:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][N:26]=1>CC(N(C)C)=O>[CH3:1][N:2]([C:25]1[N:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][N:26]=1)[CH2:3][CH2:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]([OH:13])=[O:12])[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27739122-Chloro-4-(trifluoromethyl)pyrimidineHCID 178483656HCID 178483656, compound

Product 1

HCID 178483655HCID 178483655, compoundYield 112.7%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 0.250 g (1.13 mmol) of trans-4-(2-methylamino-ethyl)-cyclohexanecarboxylic acid•HCl, 1.04 mL (6.09 mmol, 5.3 eq) of Huenig's base and 0.412 g (2.26 mmol, 2 eq) of 2-chloro-4-(trifluoromethyl)pyrimidine in 4 mL of DMA were reacted at RT for 19 h. The solvent was evaporated and the residue partitioned between Et2O (×3)/aqueous 10% KH2PO4, dried over Na2SO4, and evaporated to yield 0.422 g (quantitative) of trans-4-{2-[methyl-(4-trifluoromethyl-pyrimidin-2-yl)-amino]-ethyl}-cyclohexanecarboxylic acid, MS: 330 (M−H−), MP: 110-112° C.

Workup

  1. customThe solvent was evaporated
  2. customthe residue partitioned between Et2O (×3)/aqueous 10% KH2PO4
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-5689fc9b4ab848e7bbc656790427071b
Source dataset
uspto-grants-2008_10
Patent number
US07442791B2

Reaction notes

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