홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Sodium hydride → (+/-)-[3-((4-Methylbenzoyl)-{1-[3-(3-methyl-[1,2,4]oxadiazol-5-ylmethyl)-4-oxo-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl]propyl}-amino)-propyl]-carbamic acid tert-butyl ester

HRID 1795940
노트
인쇄 미리보기

반응식

HRID 1795940 반응식
C[O:2][C:3](=O)[CH2:4][N:5]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][N:8]2[N:7]=[C:6]1[CH:15]([N:18]([CH2:28][CH2:29][CH2:30][NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:19](=[O:27])[C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)[CH2:16][CH3:17].O[NH:41][C:42](=[NH:44])[CH3:43].[H-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[C:35]([O:34][C:32](=[O:33])[NH:31][CH2:30][CH2:29][CH2:28][N:18]([C:19](=[O:27])[C:20]1[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=1)[CH:15]([C:6]1[N:5]([CH2:4][C:3]2[O:2][N:44]=[C:42]([CH3:43])[N:41]=2)[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][N:8]2[N:7]=1)[CH2:16][CH3:17])([CH3:37])([CH3:38])[CH3:36]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 69591790(+/-)-(2-{1-[(3-tert-Butoxycarbonylaminopropyl)-(4-methylbenzoyl)-amino]-propyl}-4-oxo-4H-pyrrolo[2,1-f][1,2,4]triazin-3-yl)-acetic acid methyl esterHCID 178465666HCID 178465666, 화합물

생성물 1

HCID 69591854(+/-)-[3-((4-Methylbenzoyl)-{1-[3-(3-methyl-[1,2,4]oxadiazol-5-ylmethyl)-4-oxo-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl]propyl}-amino)-propyl]-carbamic acid tert-butyl ester수율 18%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of (±)-(2-{1-[(3-tert-butoxycarbonylaminopropyl)-(4-methylbenzoyl) amino]propyl}-4-oxo-4H-pyrrolo[2,1-f][1,2,4]triazin-3-yl)acetic acid methyl ester (Example 7 A, 26 mg, 0.05 mmol) and N-hydroxyacetamidine (Tyger Scientific, 6 mg, 0.08 mmol) in DMF (1 mL), under Ar, was treated with sodium hydride (6.5 mg as 60% dispersion in mineral oil, 0.15 mmol) and stirred at ambient temperature overnight before being diluted with ethyl acetate. The organic layer was washed twice with water and once with brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The crude product was purified by preparative HPLC (YMC S5 ODS, 20×250 mm, 30 minute gradient from 66–90% aqueous methanol with 0.1% TFA). The appropriate fractions were combined, neutralized with saturated aqueous sodium bicarbonate, and then concentrated in vacuo to remove methanol. The mixture was extracted with ethyl acetate (3×10 mL). The combined organic layers were washed once each with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to yield the title compound (5 mg, 18%): 1H NMR (CDCl3) δ 7.45 (m, 1H), 7.21–7.08 (m, 4H), 7.07 (m, 1H), 6.59 (m, 1H), 5.97 (m, 1H), 5.83 (m, 1H), 5.47 (m, 1H), 3.92 (m, 1H), 3.36 (m, 2H), 2.74 (m, 2H), 2.38 (s, 3H), 2.34 (s, 3H), 2.30–1.98 (m, 2H), 1.74–0.80 (m, 14H); MS (ESI+) 564.20 (M++H).

후처리

  1. washThe organic layer was washed twice with water and once with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by preparative HPLC (YMC S5 ODS, 20×250 mm, 30 minute gradient from 66–90% aqueous methanol with 0.1% TFA)
  5. concentrationconcentrated in vacuo
  6. customto remove methanol
  7. extractionThe mixture was extracted with ethyl acetate (3×10 mL)
  8. washThe combined organic layers were washed once each with water and brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-a281f885bcbd40a482b75bc7b92b1b55
출처 데이터셋
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07030118B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트