(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 449839ノート

反応式

HRID 449839 の反応式
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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23938Palladium触媒2 回HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

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]+

後処理

  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

出典と根拠

ORDレコード
ord-6b96c004a33e4400bf50a82ed9b59c14
出典データセット
uspto-grants-2013_07
特許番号
US08486943B2

反応ノート

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