Piperidine → HCID 86759979, compound

HRID 1795948Notes

Reaction equation

HRID 1795948 reaction equation
C1C2C(COC(=O)[NH:17][CH:18]([C:21]3[N:26]([CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:25](=[O:34])[C:24]4=[CH:35][CH:36]=[C:37]([Cl:38])[N:23]4[N:22]=3)[CH2:19][CH3:20])C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>CN(C=O)C.CCOC(C)=O>[NH2:17][CH:18]([C:21]1[N:26]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:25](=[O:34])[C:24]2=[CH:35][CH:36]=[C:37]([Cl:38])[N:23]2[N:22]=1)[CH2:19][CH3:20]

Participants

5

Reactant 2

HCID 8082PiperidineHCID 69591816HCID 69591816, compound

Product 1

HCID 86759979HCID 86759979, compoundYield 85.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (±)-[1-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-propyl]-carbamic acid 9H-fluoren-9-ylmethyl ester (0.92 g, 1.7 mmol) and piperidine (0.5 mL) in DMF (10 mL) was allowed to stand at rt for 30 min. The reaction mixture was diluted with EtOAc to 100 mL, washed with 10% LiCl solution (2×50 mL) and dried over MgSO4. Concentration and purification of the crude product by flash column chromatography (SiO2, EtOAc/hexane 1:1) gave the title compound as colorless oil (0.462 g, 85.5%): 1H NMR (CDCl3) δ 7.26 (m, 2H), 7.20 (m, 1H), 7.10 (d, 2H, J=7.15 Hz), 7.00 (d, 1H, J=4.4 Hz), 6.42 (d, 1H, J=4.4 Hz), 5.43 (d, 1H, J=16.5 Hz), 5.23 (d, 1H, J=16.5 Hz), 3.67 (t, 1H, J=6.62 Hz), 1.83 (m, 1H), 1.57 (m, 1H), 0.83 (t, 3H, J=7.15 Hz); 13C NMR (CDCl3) δ 154.6, 136.3, 129.0, 127.8, 126.3, 117.7, 117.2, 110.0, 108.4, 53.6, 44.4, 29.7, 10.5; MS (ESI+), 316.99, 319.31 (M++H).

Workup

  1. washwashed with 10% LiCl solution (2×50 mL)
  2. dry with materialdried over MgSO4
  3. concentrationConcentration and purification of the crude product by flash column chromatography (SiO2, EtOAc/hexane 1:1)

Sources & evidence

ORD record
ord-d44afc9d866a497db07e1f29e92858cf
Source dataset
uspto-grants-2006_04
Patent number
US07030118B2

Reaction notes

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