(S)-4-((4-Chloro-3-methoxypyridin-2-yl)methyl)-7-cyano-1,2,3,4-tetrahydrocyclopenta[b]indol-2-ylcarbamic acid isopropyl ester → (S)-4-((3-Methoxypyridin-2-yl)methyl)-7-cyano-1,2,3,4-tetrahydrocyclopenta[b]indol-2-ylcarbamic acid isopropyl ester

HRID 449839노트

반응식

HRID 449839 반응식
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][N:9]2[C:17]3[CH:16]=[CH:15][C:14]([C:18]#[N:19])=[CH:13][C:12]=3[C:11]3[CH2:20][C@H:21]([NH:23][C:24](=[O:29])[O:25][CH:26]([CH3:28])[CH3:27])[CH2:22][C:10]2=3)[C:3]=1[O:30][CH3:31]>[Pd].CO.O>[CH:26]([O:25][C:24](=[O:29])[NH:23][C@@H:21]1[CH2:22][C:10]2[N:9]([CH2:8][C:4]3[C:3]([O:30][CH3:31])=[CH:2][CH:7]=[CH:6][N:5]=3)[C:17]3[CH:16]=[CH:15][C:14]([C:18]#[N:19])=[CH:13][C:12]=3[C:11]=2[CH2:20]1)([CH3:28])[CH3:27]

참가 물질

5

반응물 1

HCID 66933264(S)-4-((4-Chloro-3-methoxypyridin-2-yl)methyl)-7-cyano-1,2,3,4-tetrahydrocyclopenta[b]indol-2-ylcarbamic acid isopropyl ester

생성물 1

HCID 66933193(S)-4-((3-Methoxypyridin-2-yl)methyl)-7-cyano-1,2,3,4-tetrahydrocyclopenta[b]indol-2-ylcarbamic acid isopropyl ester수율 94%

시약·촉매·용매 3

HCID 23938Palladium촉매2회HCID 887Methanol용매HCID 962Water용매

실험 절차

A mixture of (S)-isopropyl 4-((4-chloro-3-methoxypyridin-2-yl)methyl)-7-cyano-1,2,3,4-tetrahydrocyclopenta[b]indol-2-ylcarbamate (12.53 g, 28.55 mmol) and 10% palladium on carbon (1.00 g) in methanol (150 mL) is hydrogenated at 50 psi at room temperature overnight. A fresh batch of 10% palladium on carbon (1.2 g) is slurried in water (˜2 mL) and added to the reaction mixture, which is hydrogenated (50 psi) at room temperature overnight. The catalyst is filtered off and the solution is concentrated under reduced pressure to obtain a pale yellow solid. The solid is triturated with ether twice and dried under high vacuum to afford a yellow solid (10.80 g, 94%). LC-ES/MS m/z 405.2 [M+H]+

후처리

  1. additionadded to the reaction mixture, which
  2. customat room temperature
  3. customovernight
  4. filtrationThe catalyst is filtered off
  5. concentrationthe solution is concentrated under reduced pressure
  6. customto obtain a pale yellow solid
  7. customThe solid is triturated with ether twice
  8. customdried under high vacuum

출처 및 근거

ORD 기록
ord-6b96c004a33e4400bf50a82ed9b59c14
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486943B2

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