Diisopropylethylamine → HCID 178432790, compound

HRID 967226Notes

Reaction equation

HRID 967226 reaction equation
[CH3:1][N:2]([CH2:16][C@H:17]1[CH2:22][CH2:21][C@H:20]([CH2:23][O:24][CH2:25]/[CH:26]=[CH:27]/[CH2:28][NH:29][CH3:30])[CH2:19][CH2:18]1)[S:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=1)(=[O:5])=[O:4].Cl[C:32]1[CH:37]=[CH:36][N:35]=[C:34]([CH3:38])[N:33]=1.C(N(C(C)C)C(C)C)C>CN(C)C=O>[CH3:1][N:2]([CH2:16][C@H:17]1[CH2:22][CH2:21][C@H:20]([CH2:23][O:24][CH2:25]/[CH:26]=[CH:27]/[CH2:28][N:29]([CH3:30])[C:32]2[CH:37]=[CH:36][N:35]=[C:34]([CH3:38])[N:33]=2)[CH2:19][CH2:18]1)[S:3]([C:6]1[CH:7]=[CH:8][C:9]([C:12]([F:15])([F:13])[F:14])=[CH:10][CH:11]=1)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 4244474-Chloro-2-methylpyrimidineHCID 178483583HCID 178483583, compound

Product 1

HCID 178432790HCID 178432790, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 77 mg (0.17 mmol) trans-N-methyl-N-[4-(4-methylamino-(E)-but-2-enyloxymethyl)-cyclohexylmethyl]-4-trifluoromethyl-benzenesulfonamide (example 20.6), 0.044 g (0.34 mmol) of 4-chloro-2-methyl-pyrimidine [Ger. Offen. (1990), DE3905364 A1] and 0.06 ml (0.34 mmol) N-ethyl-diisopropylamine in 1 ml of N,N-dimethylformamide was stirred for 2 hours at 80° C. The reaction mixture was then cooled to room temperature, poured into 30 ml of ice-water and extracted 3 times with 10 ml of ether. The combined ether phases were washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue formed was chromatographed on silica gel with a 95:5:1 v/v/v mixture of dichloromethane, methanol and saturated aqueous ammonia as the eluent giving 55 mg (59%) trans-N-methyl-N-(4-{4-[methyl-(2-methyl-pyrimidin-4-yl)-amino]-(E)-but-2-enyloxymethyl}-cyclohexylmethyl)-4-trifluoromethyl-benzenesulfonamide as yellowish viscous oil, MS: 541 (MH+).

Workup

  1. extractionextracted 3 times with 10 ml of ether
  2. washThe combined ether phases were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue formed
  6. customwas chromatographed on silica gel with a 95:5:1 v/v/v mixture of dichloromethane, methanol and saturated aqueous ammonia as the eluent

Sources & evidence

ORD record
ord-2a2e7f47b8d247cd959d37e9ba4afb20
Source dataset
uspto-grants-2005_10
Patent number
US06953806B2

Reaction notes

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