Triethylamine → HCID 44218583, compound

HRID 1931508Notes

Reaction equation

HRID 1931508 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([NH:13][C@H:14]1[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][CH2:15]1)[CH:7]=[CH:6]2.C(N(CC)CC)C.[F:30][C:31]1[CH:39]=[CH:38][C:34]([C:35](Cl)=[O:36])=[CH:33][CH:32]=1>O1CCCC1>[F:30][C:31]1[CH:39]=[CH:38][C:34]([C:35]([NH:1][CH2:2][C:3]2[CH:4]=[C:5]3[C:10](=[CH:11][CH:12]=2)[N:9]=[C:8]([NH:13][C@H:14]2[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH2:16][CH2:15]2)[CH:7]=[CH:6]3)=[O:36])=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 68628477HCID 68628477, compound

Product 1

HCID 44218583HCID 44218583, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (ice bath) and stirred solution of (6-aminomethyl-quinolin-2-yl)-(R)-indan-1-yl-amine (130 mg, 0.45 mmol) and triethyl amine (50 mg, 0.49 mmol) in tetrahydrofurane (2.6 ml) was added 4-fluorobenzoyl chloride (78 mg, 0.49 mmol) and the mixture was allowed to stir at room temperature for 1 h. Evaporation and purification by flash chromatography (ethyl acetate/heptane) on silica gel yielded the title compound as white foam (150 mg, 81%). MS: m/e=412.2 (M+H+).

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-3af547fd240248bcbd96ec87855a7cf7
Source dataset
uspto-grants-2012_05
Patent number
US08188284B2

Reaction notes

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