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 1795986노트

반응식

HRID 1795986 반응식
[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

참가 물질

5

반응물 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

생성물 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 ester수율 44%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-131efe79b1fd48278b7296316573718a
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07030118B2

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