Water → HCID 86683046, compound

HRID 1497225Notes

Reaction equation

HRID 1497225 reaction equation
Cl[C:2]1[C:11]([C:12]#[N:13])=[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]([CH3:22])[CH3:21])[CH:15]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:23])[CH:8]=2)[N:3]=1.[CH2:24]([NH:26][CH2:27][CH3:28])[CH3:25].C(N(CC)CC)C.O>CN(C=O)C>[Cl:23][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([N:26]([CH2:27][CH3:28])[CH2:24][CH3:25])[C:11]([C:12]#[N:13])=[C:10]2[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]([CH3:22])[CH3:21])[CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8021DiethylamineHCID 8471TriethylamineHCID 86683045HCID 86683045, compound

Product 1

HCID 86683046HCID 86683046, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2,6-dichloro-4-(3-isopropyl-phenyl)-quinoline-3-carbonitrile (128 mg, 375 μmol, Eq: 1.00), diethylamine (54.9 mg, 78.4 μl, 750 μmol, Eq: 2) and triethylamine (114 mg, 157 μl, 1.13 mmol, Eq: 3) in DMF (1 ml) was heated first to 120° C. for 20 min and then to 180° C. for additional 20 min in a microwave. Then water was added and the mixture was extracted with ethyl acetate (3×). The combined extracts were washed with water and brine, dried with Na2SO4 and evaporated. The remaining residue was purified by column chromatography (silica gel, heptane/EtOAc 90:10 to 85:15) to afford the title compound as yellow oil (128 mg). MS (ESI): 377.1 (M−H)−.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×)
  2. washThe combined extracts were washed with water and brine
  3. dry with materialdried with Na2SO4
  4. customevaporated
  5. customThe remaining residue was purified by column chromatography (silica gel, heptane/EtOAc 90:10 to 85:15)

Sources & evidence

ORD record
ord-f83912d88b6a48f18c00103a626146a9
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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