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 1795992ノート

反応式

HRID 1795992 の反応式
[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

参加物

7

反応物 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

生成物 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 ester収率 32%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6d8f0421cab4442da12ee4b607435951
出典データセット
uspto-grants-2006_04
特許番号
US07030118B2

反応ノート

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