Triethylamine → N-[3-(3-chloro-5-cyano-2-methyl-1H-pyrrol-1-yl)-1-methylpropyl]-2-cyano-3,4,4-trimethylpentanamide

HRID 1271455Notes

Reaction equation

HRID 1271455 reaction equation
[C:1]([CH:3]([CH:7]([CH3:12])[C:8]([CH3:11])([CH3:10])[CH3:9])[C:4]([OH:6])=O)#[N:2].[NH2:13][CH:14]([CH3:26])[CH2:15][CH2:16][N:17]1[C:21]([CH3:22])=[C:20]([Cl:23])[CH:19]=[C:18]1[C:24]#[N:25].C(N(CC)CC)C>S(Cl)(Cl)=O.C(OCC)(=O)C>[Cl:23][C:20]1[CH:19]=[C:18]([C:24]#[N:25])[N:17]([CH2:16][CH2:15][CH:14]([NH:13][C:4](=[O:6])[CH:3]([C:1]#[N:2])[CH:7]([CH3:12])[C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:26])[C:21]=1[CH3:22]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 218952532-Cyano-3,4,4-trimethylpentanoic acidHCID 218952681-(3-aminobutyl)-4-chloro-5-methyl-1H-pyrrole-2-carbonitrile

Product 1

HCID 21895244N-[3-(3-chloro-5-cyano-2-methyl-1H-pyrrol-1-yl)-1-methylpropyl]-2-cyano-3,4,4-trimethylpentanamide

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 24386Thionyl ChlorideSolvent2×

Procedure

A solution of 0.54 g (3.5 mmol) 2-cyano-3,4,4-trimethylpentanoic acid in 15 mL thionyl chloride was heated at reflux for 30 min. The thionyl chloride was stripped and the residue was dried in vacuo. The residue was then dissolved in 20 mL methylene chloride and a solution of 0.66 g (3.13 mmol) of 1-(3-aminobutyl)-4-chloro-5-methyl-1H-pyrrole-2-carbonitrile and 0.59 mL (4.2 mmol) triethylamine was added dropwise. The mixture was stirred at room temperature overnight. Solvent was stripped and the residue was taken up in ethyl acetate which was washed with water and brine. Drying (MgSO4) and removal of solvent gave an oil which was chromatographed (40% ether in hexanes) on silica gel to give the title compound as a mixture of diastereomers, mp 111–118° C. 1H NMR (CDCl3) δ 1.0 (m, 3H), 1.2–1.3 (2m, 6H), 1.4 (d, 1H), 1.6 (m, 2H), 1.9 (m, 2H), 2.2 (m, 3H), 4.1 (2m, 2H), 5.7 (m, 1H), 6.65 (2s, 1H).

Workup

  1. temperatureat reflux for 30 min
  2. customthe residue was dried in vacuo
  3. dissolutionThe residue was then dissolved in 20 mL methylene chloride
  4. washwas washed with water and brine
  5. customDrying
  6. custom(MgSO4) and removal of solvent
  7. customgave an oil which
  8. customwas chromatographed (40% ether in hexanes) on silica gel

Sources & evidence

ORD record
ord-6e0f56cc382b49d190ce2c5ea8a963ed
Source dataset
uspto-grants-2007_04
Patent number
US07205331B2

Reaction notes

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