Triethylamine → HCID 24991198, compound

HRID 1170180Notes

Reaction equation

HRID 1170180 reaction equation
[NH2:1][CH2:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7]([NH:13][CH2:14][C:15]1[O:16][C:17]([CH3:20])=[CH:18][CH:19]=1)=[N:8]2.C(N(CC)CC)C.[F:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1>C1COCC1>[F:28][C:29]1[CH:37]=[CH:36][C:32]([C:33]([NH:1][CH2:2][C:3]2[CH:12]=[CH:11][CH:10]=[C:9]3[C:4]=2[CH:5]=[CH:6][C:7]([NH:13][CH2:14][C:15]2[O:16][C:17]([CH3:20])=[CH:18][CH:19]=2)=[N:8]3)=[O:34])=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 68437142HCID 68437142, compound

Product 1

HCID 24991198HCID 24991198, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (ice bath) and stirred solution of (5-aminomethyl-quinolin-2-yl)-(5-methyl-furan-2-ylmethyl)-amine (95 mg, 0.355 mmol) and triethyl amine (39.6 mg, 0.39 mmol) in THF (2 ml) was added 4-fluorobenzoyl chloride (62 mg, 0.39 mmol) and the mixture was allowed to stir at room temperature for 16 h. Evaporation and purification by flash chromatography (ethyl acetate/heptane) on silica gel yielded the title compound as off-white solid (67 mg, 48%).

Workup

  1. temperatureTo a cooled (ice bath)
  2. customEvaporation and purification by flash chromatography (ethyl acetate/heptane) on silica gel

Sources & evidence

ORD record
ord-fed375d177d642d182dae43d88812f64
Source dataset
uspto-grants-2010_11
Patent number
US07825253B2

Reaction notes

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