Water → HCID 41121420, compound

HRID 1349520Notes

Reaction equation

HRID 1349520 reaction equation
[CH3:1][C@H:2]1[CH2:11][C@@H:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.C(N([CH:25]([CH3:27])C)CC)(C)C.[O:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[C:33](Cl)=[O:34].[OH2:36]>ClCCl>[O:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[C:33]([N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C@H:10]([N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:25](=[O:36])[CH3:27])[CH2:11][C@@H:2]1[CH3:1])=[O:34]

Participants

6

Reactant 4

HCID 962WaterHCID 682422-Furancarbonyl chlorideHCID 81531DiisopropylethylamineHCID 715776HCID 715776, compound

Product 1

HCID 41121420HCID 41121420, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (±)-cis-(2-Methyl-1,2,3,4-tetrahydro-quinolin-4-yl)-phenyl-amine (430 mg, 1.83 mmol) in dichloromethane (18 mL) at room temperature was added diisopropylethylamine (318 uL, 1.83 mmol) followed by 2-furoyl chloride. It was allowed to let stir at room temperature for 12 h. The mixture was poured into water and extracted with dichloromethane. The extracts were washed with 1 M(aq) NaOH and brine, dried over magnesium sulfate, filtered and concentrated. The crude residue was purified by silica gel chromatography (80% hexanes/20% ethyl acetate) to afford the amide (500 mg, 83%).

Workup

  1. extractionextracted with dichloromethane
  2. washThe extracts were washed with 1 M(aq) NaOH and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by silica gel chromatography (80% hexanes/20% ethyl acetate)

Sources & evidence

ORD record
ord-ad90c3f0c5d54fc39221569470e2c520
Source dataset
uspto-grants-2007_05
Patent number
US07211672B2

Reaction notes

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