Реакция #1973921

Уравнение реакции

water

N-cyclopropyl-2-(2,5-dichloropyrimidin-4-yl)-1-(ethoxymethyl)-1H-indole-4-carboxamide

(1S,2R)-2-aminocyclopentanol hydrochloride

DIPEA

→

2-{5-chloro-2-[(1R,2S)-2-hydroxycyclopentylamino]pyrimidin-4-yl}-N-cyclopropyl-1-(ethoxymethyl)-1H-indole-4-carboxamide

Выход 60.3%

Растворители

DMSO

Условия реакции

Обработка

1. 1
   Экстракцияextracted with EA
2. 2
   ПромывкаThe combined extracts are washed with aqueous saturated sodium chloride
3. 3
   Сушкаdried over Na2SO4
4. 4
   Концентрированиеconcentrated in vacuo
5. 5
   ДругоеThe residue is purified by chromatography on silica gel

Методика

A mixture of N-cyclopropyl-2-(2,5-dichloropyrimidin-4-yl)-1-(ethoxymethyl)-1H-indole-4-carboxamide (10 g, 25 mmol), (1S,2R)-2-aminocyclopentanol hydrochloride (4.1 g, 30 mmol) and DIPEA (5 mL, 30 mmol) in DMSO (70 mL) is stirred at 100° C. for 3 h, then poured into water and extracted with EA. The combined extracts are washed with aqueous saturated sodium chloride, dried over Na2SO4 and concentrated in vacuo. The residue is purified by chromatography on silica gel to give 2-{5-chloro-2-[(1R,2S)-2-hydroxycyclopentylamino]pyrimidin-4-yl}-N-cyclopropyl-1-(ethoxymethyl)-1H-indole-4-carboxamide (7 g, 60.3%). MS (m/z): 470 (35Cl) and 472 (37Cl) (M+H)+

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