Acetic Acid → (+/-)-{3-[1-(3-Benzyl-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-propylamino]-propyl}-carbamic acid 9H-fluoren-9-ylmethyl ester

HRID 1795992노트

반응식

HRID 1795992 반응식
[NH2:1][CH:2]([C:5]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9](=[O:18])[C:8]2=[CH:19][CH:20]=[CH:21][N:7]2[N:6]=1)[CH2:3][CH3:4].C(O)(=O)C.[CH:26]1[C:38]2[CH:37]([CH2:39][O:40][C:41](=[O:47])[NH:42][CH2:43][CH2:44][CH:45]=O)[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:30]=2[CH:29]=[CH:28][CH:27]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.O1CCOCC1>[CH:35]1[C:36]2[CH:37]([CH2:39][O:40][C:41](=[O:47])[NH:42][CH2:43][CH2:44][CH2:45][NH:1][CH:2]([C:5]3[N:10]([CH2:11][C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:9](=[O:18])[C:8]4=[CH:19][CH:20]=[CH:21][N:7]4[N:6]=3)[CH2:3][CH3:4])[C:38]3[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:31]=2[CH:32]=[CH:33][CH:34]=1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 11277844Carbamic acid, (3-oxopropyl)-, 9H-fluoren-9-ylmethyl esterHCID 221799762-(1-amino-propyl)-3-benzyl-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one

생성물 1

HCID 69591775(+/-)-{3-[1-(3-Benzyl-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-propylamino]-propyl}-carbamic acid 9H-fluoren-9-ylmethyl ester수율 32%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

실험 절차

A mixture of 2-(1-amino-propyl)-3-benzyl-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one (180 mg, 0.64 mmol), acetic acid (Example 26, 65 μl, 0.95 mmol), 3-oxo-propyl-carbamic acid 9H-fluoren-9-ylmethyl ester (Org. Lett. 2002, 4, 3001–3003), 1,4-dioxane (5 mL), and 4 Å molecular sieves was stirred at room temperature for 15 min then treated with sodium triacetoxyborohydride (112 mg, 0.53 mmol). After 45 min, the reaction was diluted with methylene chloride (25 mL), filtered, washed with saturated sodium bicarbonate, dried (MgSO4) and concentrated. The residue was purified by flash column chromatography on silica gel eluting with ethyl acetate/hexanes to give the desired compound (170 mg, 32%): MS (ESI+) 562.2 (M++H).

후처리

  1. waitAfter 45 min
  2. filtrationfiltered
  3. washwashed with saturated sodium bicarbonate
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography on silica gel eluting with ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-6d8f0421cab4442da12ee4b607435951
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07030118B2

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