Triethylamine → HCID 25015980, compound

HRID 2076328Notes

Reaction equation

HRID 2076328 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][C@H:14]1[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][CH2:15]1)=[N:8]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:12]=[CH:11][CH:10]=[C:9]3[C:4]=2[CH:5]=[CH:6][C:7]([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)=[N:8]3)=[O:36])=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 44219394HCID 44219394, compound

Product 1

HCID 25015980HCID 25015980, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (ice bath) and stirred solution of (5-aminomethyl-quinolin-2-yl)-(R)-indan-1-yl-amine (100 mg, 0.345 mmol) and triethyl amine (38 mg, 0.38 mmol) in tetrahydrofuran (THF) (2 ml) was added 4-fluorobenzoyl chloride (60 mg, 0.38 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 white solid (90 mg, 63%). M.p. 145° C.; MS: m/e=412.3 (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-9dc03b037925409583d5fce3676bcf89
Source dataset
uspto-grants-2011_04
Patent number
US07923561B2

Reaction notes

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