tert-Butyl (S)-3-(5-(1-(((benzyloxy)carbonyl)amino)ethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate → tert-Butyl 3-(5-((S)-1-aminoethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)pyrrolidine-1-carboxylate

HRID 2205611ノート

反応式

HRID 2205611 の反応式
C(OC([NH:11][C@H:12]([C:14]1[N:19]=[C:18]2[CH:20]=[CH:21][N:22]([CH3:23])[C:17]2=[CH:16][C:15]=1[C:24]1[CH2:25][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:27][CH:28]=1)[CH3:13])=O)C1C=CC=CC=1>CCO.[Pd]>[NH2:11][C@H:12]([C:14]1[N:19]=[C:18]2[CH:20]=[CH:21][N:22]([CH3:23])[C:17]2=[CH:16][C:15]=1[CH:24]1[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:30])[CH2:25]1)[CH3:13]

参加物

4

反応物 1

HCID 118214749tert-Butyl (S)-3-(5-(1-(((benzyloxy)carbonyl)amino)ethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate

生成物 1

HCID 118207715tert-Butyl 3-(5-((S)-1-aminoethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)pyrrolidine-1-carboxylate収率 54%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

反応条件

温度
27 °C

実験手順

A mixture of tert-butyl (S)-3-(5-(1-(((benzyloxy)carbonyl)amino)ethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate (900 mg, 1.89 mmol) and Pd/C (100 mg) in EtOH (50 mL) was stirred at 27° C. for 3 hours under H2 (50 psi). The reaction mixture was subsequently filtered, and the filtrate was concentrated to dryness. The residue was purified by preparative HPLC to afford a mixture of the diastereomers of the title compound as a yellow oil (350 mg, 54%). 1H NMR (400 MHz, CDCl3) δ ppm 7.44 (d, J=6.4 Hz, 1H), 7.22 (d, J=3.2 Hz, 1H), 6.61 (d, J=3.2 Hz, 1H), 4.51 (q, J=6.4 Hz, 1H), 3.86-3.37 (m, 1H), 3.76 (s, 3H), 2.31-2.30 (m, 1H), 1.50 (s, 9H), 1.44 (d, J=6.4 Hz, 3H); ESI-MS m/z [M+H]+ calc'd for C19H28N4O2, 345. found 345.

後処理

  1. filtrationThe reaction mixture was subsequently filtered
  2. concentrationthe filtrate was concentrated to dryness
  3. customThe residue was purified by preparative HPLC
  4. customto afford

出典と根拠

ORDレコード
ord-6b4fad31638e4dcc89aac73f8b098ee9
出典データセット
uspto-grants-2016_06
特許番号
US09371321B2

反応ノート

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