Triethylamine → HCID 131720207, compound

HRID 1379281Notes

Reaction equation

HRID 1379281 reaction equation
[CH3:1][NH:2][CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][N:9]=2)[C:4]1=[O:18].C(N(CC)CC)C.[CH3:26][C:27]([CH3:33])([CH3:32])[CH2:28][C:29](Cl)=[O:30]>ClCCl>[CH3:26][C:27]([CH3:33])([CH3:32])[CH2:28][C:29]([N:2]([CH3:1])[CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][N:9]=2)[C:4]1=[O:18])=[O:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 815143,3-Dimethylbutanoyl chlorideHCID 22909965HCID 22909965, compound

Product 1

HCID 131720207HCID 131720207, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred solution of 3-methylamino-1(4-trifluoromethylpyridin-2-yl)pyrrolidin-2-one (0.30 g, prepared as described in Example 7, Step 3, above) in dichloromethane (20 ml) was treated successively with triethylamine (0.13 g) and 3,3-dimethylbutanoyl chloride (0.16 g). After one hour, the mixture was diluted with dichloromethane, washed with water and brine, dried over magnesium sulphate and evaporated under reduced pressure. The residue was chromatographed on silica, using hexane-ethyl acetate (1:1) as eluant, to give Compound 28 (0.31 g, m.p. 47°-53° C.). NMR (CDCl3): δ 1.31(9H,s); 2.31(4H,m+s); 3.09(3H,s); 3.88(1H,m); 4.32(1H,m); 5.22(1H,t); 7.26(1H,dd); 8.52(1H,d); 8.78(1H,s). MS: M+357.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over magnesium sulphate
  3. customevaporated under reduced pressure
  4. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-5638cd4999c541efb9eb0078be916e4c
Source dataset
uspto-grants-1997_09
Patent number
US05670656

Reaction notes

Loading…