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Cyclopentanone → (+/-)-3-Benzyl-2-(1-cyclopentylamino-propyl)-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one

HRID 1795991
Notes
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Reaction equation

HRID 1795991 reaction equation
[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:22]1(=O)[CH2:26][CH2:25][CH2:24][CH2:23]1.C([O-])(=O)C.[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCOCC1>[CH2:11]([N:10]1[C:9](=[O:18])[C:8]2=[CH:19][CH:20]=[CH:21][N:7]2[N:6]=[C:5]1[CH:2]([NH:1][CH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)[CH2:3][CH3:4])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8452Cyclopentanone2×HCID 517045Sodium AcetateHCID 5049666Sodium triacetoxyborohydride2×HCID 221799762-(1-amino-propyl)-3-benzyl-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one

Product 1

HCID 22180088(+/-)-3-Benzyl-2-(1-cyclopentylamino-propyl)-3H-pyrrolo[2,1-f][1,2,4]triazin-4-oneYield 71.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-(1-amino-propyl)-3-benzyl-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one (Example 26, 50 mg, 0.16 mmol), cyclopentanone (13 mg, 0.16 mmol), anhydrous sodium acetate (26 mg, 0.32 mmol), 4 Å molecular sieves (50 mg) and 1,4-dioxane (10 mL) was stirred at room temperture for 40 min. The mixture was treated with sodium triacetoxyborohydride (51 mg, 0.24 mmol) in one portion and stirred at room temperature for 40 h. Additional portions of cyclopentanone (0.16 mmol) and sodium triacetoxyborohydride (0.16 mmol) were added to the mixture which was stirred for an additional 3.5 hours then filtered. The filtrate was partitioned between ethyl acetate and saturated sodium bicarbonate, the ethyl acetate phase washed with brine, dried (MgSO4) and concentrated. The residue was purified by flash column chromatography on silica gel eluting with ethyl acetate to give the title compound (40 mg, 71%): 1H NMR (DMSO-d6) δ 0.88 (t, 3H, J=7.15 Hz), 0.95 (m, 1H), 1.05 (m, 1H), 1.20 (m, 1H), 1.31 (m, 1H), 1.33 (m, 1H), 1.50–1.72 (m, 6H), 2.72 (m, 1H), 3.53 (m, 1H), 4.95 (m, 1H), 5.58 (m, 1H), 6.54 (s, 1H), 7.08 (s, 1H) 7.16 (s 2H), 7.24–7.35 (m, 3H), 7.35 (s, 1H).

Workup

  1. stirringstirred at room temperature for 40 h
  2. stirringwas stirred for an additional 3.5 hours
  3. filtrationthen filtered
  4. customThe filtrate was partitioned between ethyl acetate and saturated sodium bicarbonate
  5. washthe ethyl acetate phase washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-1c4a5ba7bde74080b80ad17bd5554182
Source dataset
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07030118B2

Reaction notes

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