Réaction #7278

Équation de réaction

N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

N-(tert-butoxycarbonyl)-L-proline

N,N-diisopropylethylamine

1-hydroxybenzotriazole hydrate

1-(3-dimethylaminopropyl)-3-ethyl carbodiimide HCl

→

amide

Rendement 116.9%

(S)-Pyrrolidine-2-carboxylic acid 4-{[(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide

Rendement 116.9%

Solvants

CH2Cl2

sodium bicarbonate

CH2Cl2

Conditions de réaction

Traitement

1. 1
   Autrethe aqueous layer was separated
2. 2
   Extractionextracted with CH2Cl2 (2×15 mL)
3. 3
   SéchageThe combined organic phases were dried (Na2SO4)
4. 4
   Filtrationfiltered
5. 5
   Autreevaporated in vacuo
6. 6
   Autreto give the crude product as a white foam
7. 7
   AutrePurification by column chromatography on silica gel (CH2Cl2/MeOH, 96:4)

Mode opératoire

To a stirred solution of N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (148 mg, 0.37 mmol) in dry CH2Cl2 (5 mL) was added N-(tert-butoxycarbonyl)-L-proline (88 mg, 0.41 mmol), N,N-diisopropylethylamine (0.13 mL, 0.75 mmol), 1-hydroxybenzotriazole hydrate (68 mg, 0.50 mmol) and 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide HCl (EDC) (99 mg, 0.52 mmol) and the mixture stirred at room temperature overnight. The reaction mixture was diluted with CH2Cl2 (25 mL) and saturated aqueous sodium bicarbonate (30 mL) and the aqueous layer was separated and extracted with CH2Cl2 (2×15 mL). The combined organic phases were dried (Na2SO4), filtered and evaporated in vacuo to give the crude product as a white foam. Purification by column chromatography on silica gel (CH2Cl2/MeOH, 96:4) gave the desired amide (214 mg, 85%) as a white foam.

Source