Реакция #168456

Уравнение реакции

TBAF

3-{4-[2-(2-{[tert-butyl(dimethyl)silyl]oxy]ethoxy)-5-chloropyridin-3-yl}-2-[(trans)-hexahydrocyclopenta[b][1,4]oxazin-4(4aH)-yl]-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridin-6-yl}-1,2,4-oxadiazol-5(4H)-one

→

3-{4-[5-chloro-2-(2-hydroxyethoxy)pyridin-3-yl]-2-[(trans)-hexahydrocyclopenta[b][1,4]oxazin-4(4aH)-yl]-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-d]pyridin-6-yl}-1,2,4-oxadiazol-5(4H)-one

Растворители

THF

Условия реакции

Обработка

1. 1
   КонцентрированиеThe reaction was concentrated
2. 2
   workup.DISSOLUTIONthe residue was dissolved in CH2Cl2/IPA (4:1, 15 mL)
3. 3
   Промывкаwashed twice using water (10 mL)
4. 4
   ДругоеThe layers were separated
5. 5
   Концентрированиеthe organic layer was concentrated under reduced pressure
6. 6
   ДругоеPurification of the residue on a silica gel column with 0 to 10% MeOH/CH2Cl2

Методика

TBAF (0.1 mL, 1 M in THF, 0.1 mmol) was added to solution of 3-{4-[2-(2-{[tert-butyl(dimethyl)silyl]oxy]ethoxy)-5-chloropyridin-3-yl}-2-[(trans)-hexahydrocyclopenta[b][1,4]oxazin-4(4aH)-yl]-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridin-6-yl}-1,2,4-oxadiazol-5(4H)-one (racemic, 20 mg, 0.027 mmol) in THF (1.0 mL) at room temperature and stirred for 16 hours. The reaction was concentrated, and the residue was dissolved in CH2Cl2/IPA (4:1, 15 mL) and washed twice using water (10 mL). The layers were separated, and the organic layer was concentrated under reduced pressure. Purification of the residue on a silica gel column with 0 to 10% MeOH/CH2Cl2 afforded 3-{4-[5-chloro-2-(2-hydroxyethoxy)pyridin-3-yl]-2-[(trans)-hexahydrocyclopenta[b][1,4]oxazin-4(4aH)-yl]-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-d]pyridin-6-yl}-1,2,4-oxadiazol-5(4H)-one (racemic). 1H NMR (400 MHz, CDCl3) δ 8.28 (br s, 2H), 7.26 (s, 1H), 4.70 (d, J=10.2 Hz, 1H), 3.90 (t, J=12.2 Hz, 2H), 3.70-3.80 (m, 3H), 3.45-3.74 (m, 2H), 3.17-3.32 (m, 2H), 3.10 (t, J=12.4 Hz, 2H), 2.39 (m, 1H), 1.99 (m, 1H), 1.88 (m, 1H), 1.66-1.76 (m, 2H), 1.45-1.62 (m, 6H), 1.02-1.32 (m, 2H), 0.88 (m, 1H), 0.77 (d, J=7.4 Hz, 3H), 0.42-0.60 (m, 2H). MS ES calc'd. for C30H36ClN7O5 [M−1]− 608. found 608.

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