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 2205611노트

반응식

HRID 2205611 반응식
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]

참가 물질

4

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

반응 조건

온도
27 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6b4fad31638e4dcc89aac73f8b098ee9
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09371321B2

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