Sodium triacetoxyborohydride → (+/-)-(3-{[1-(3-benzyl-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-propyl]-cyclohexyl-amino}-propyl)-carbamic acid 9H-fluoren-9-ylmethyl ester

HRID 1795986ノート

反応式

HRID 1795986 の反応式
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17][N:11]2[N:10]=[C:9]1[CH:18]([NH:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[CH2:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:28]1[C:40]2[CH:39]([CH2:41][O:42][C:43](=[O:49])[NH:44][CH2:45][CH2:46][CH:47]=O)[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32]=2[CH:31]=[CH:30][CH:29]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH:37]1[C:38]2[CH:39]([CH2:41][O:42][C:43](=[O:49])[NH:44][CH2:45][CH2:46][CH2:47][N:21]([CH:18]([C:9]3[N:8]([CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[C:13](=[O:14])[C:12]4=[CH:15][CH:16]=[CH:17][N:11]4[N:10]=3)[CH2:19][CH3:20])[CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[C:40]3[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:33]=2[CH:34]=[CH:35][CH:36]=1

参加物

5

反応物 3

HCID 5049666Sodium triacetoxyborohydrideHCID 11277844Carbamic acid, (3-oxopropyl)-, 9H-fluoren-9-ylmethyl esterHCID 221800673-Benzyl-2-(1-cyclohexylamino-propyl)-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one

生成物 1

HCID 69591832(+/-)-(3-{[1-(3-benzyl-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-propyl]-cyclohexyl-amino}-propyl)-carbamic acid 9H-fluoren-9-ylmethyl ester収率 44%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

A mixture of 3-benzyl-2-(1-cyclohexylamino-propyl)-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one (Example 28, 150 mg, 0.41 mmol), (3-oxo-propyl)-carbamic acid 9H-fluoren-9-ylmethyl ester (Org. Lett. 2002, 4, 3001–3003, 184 mg, 0.62 mmol), acetic acetic (1.5 eq), 4 Å molecular sieves (100 mg), and 1,2-dichloroethane (10 mL) was stirred at room temperature for 30 min, then treated with sodium triacetoxyborohydride (130 mg, 0.62 mmol). After 3 h, the mixture was filtered and the filtrate washed with saturated sodium bicarbonate and water, dried (MgSO4), and concentrated. The residue was purified by flash column chromatography on silica gel eluting with ethyl acetate/hexanes to give the title compound as a white solid (115 mg, 44%): MS (ESI+) 644.44 (M++H).

後処理

  1. waitAfter 3 h
  2. filtrationthe mixture was filtered
  3. washthe filtrate washed with saturated sodium bicarbonate and water
  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-131efe79b1fd48278b7296316573718a
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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