Hydrochloric Acid → (3-Chloropyrazin-2-yl)(2-phenylquinolin-7-yl)methanamine

HRID 1894926Notes

Reaction equation

HRID 1894926 reaction equation
COC1C=CC(C(C2C=CC(OC)=CC=2)=[N:10][CH2:11][C:12]2[CH:21]=[C:20]3[C:15]([CH:16]=[CH:17][C:18]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[N:19]3)=[CH:14][CH:13]=2)=CC=1.C[Si](C)(C)N[Si](C)(C)C.[Na].Cl[C:47]1[C:52]([Cl:53])=[N:51][CH:50]=[CH:49][N:48]=1.Cl>C1COCC1>[Cl:53][C:52]1[C:47]([CH:11]([NH2:10])[C:12]2[CH:21]=[C:20]3[C:15]([CH:16]=[CH:17][C:18]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[N:19]3)=[CH:14][CH:13]=2)=[N:48][CH:49]=[CH:50][N:51]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 13838HexamethyldisilazaneHCID 785752,3-DichloropyrazineHCID 5360545SodiumHCID 86662309HCID 86662309, compound

Product 1

HCID 51051365(3-Chloropyrazin-2-yl)(2-phenylquinolin-7-yl)methanamineYield 87.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-5 °C

Procedure

N-[bis(4-methoxyphenyl)methylidene]-1-(2-phenylquinolin-7-yl)methanamine (100 mg, 0.22 mmol) was added to a flask and protected by nitrogen. THF (2 mL) was added and a clear solution was obtained. The solution was cooled to −5° C. and then 1.0 M 1,1,1,3,3,3-hexamethyldisilazane, sodium salt in THF (0.26 mL, 0.26 mol) was added. After 20 min, 2,3-dichloropyrazine (36 mg, 0.24 mmol) in THF (1.0 mL) was added. After a further 20 min, 2M HCl (2 mL) was added and the mixture was stirred at room temperature for 10 min. The aqueous mixture was washed with DCM (3×) and then basified to pH 10 with solid potassium carbonate. A white solid precipitated from the aqueous solution and the resulting suspension was extracted with DCM. The organic solution was washed with water, dried over sodium sulfate, filtered, and concentrated in vacuo to give a light yellow oil (67 mg). The yellow oil was further purified by silica gel chromatography (eluted with ethyl acetate/methanol/triethylamine, 10:0.5:1) to yield a colorless oil (63 mg, 83% yield).

Workup

  1. customa clear solution was obtained
  2. waitAfter a further 20 min
  3. washThe aqueous mixture was washed with DCM (3×)
  4. customA white solid precipitated from the aqueous solution
  5. extractionthe resulting suspension was extracted with DCM
  6. washThe organic solution was washed with water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-243ef9c0544b48fb841fc3f93876b3ef
Source dataset
uspto-grants-2013_08
Patent number
US08513415B2

Reaction notes

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