تفاعل #1973922

معادلة التفاعل

water

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

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

DIPEA

→

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

المردود 93.6%

المذيبات

DMSO

ظروف التفاعل

المعالجة

1. 1
   استخلاصextracted with EA (2×500 mL)
2. 2
   غسيلThe combined extracts are washed with aqueous saturated sodium chloride (500 mL)
3. 3
   تجفيفdried over Na2SO4
4. 4
   تركيزconcentrated in vacuo
5. 5
   أخرىThe residue is purified by chromatography on silica gel

الإجراء التجريبي

A mixture of N-cyclopropyl-2-(2,5-dichloropyrimidin-4-yl)-1-(ethoxymethyl)-1H-indole-4-carboxamide (30 g, 75 mmol), (1R,2R)-2-aminocyclopentanol hydrochloride (12.3 g, 90 mmol) and DIPEA (37.5 mL, 225 mmol) in DMSO (150 mL) is stirred at 80° C. for 16 h, then poured into water (1 L), and extracted with EA (2×500 mL). The combined extracts are washed with aqueous saturated sodium chloride (500 mL), dried over Na2SO4 and concentrated in vacuo. The residue is purified by chromatography on silica gel to give 2-{5-chloro-2-[(1R,2R)-2-hydroxycyclopentylamino]pyrimidin-4-yl}-N-cyclopropyl-1-(ethoxymethyl)-1H-indole-4-carboxamide (33 g, 93%). MS (m/z): 470 (35Cl) and 472 (37Cl) (M+H)+.

المصدر