1H-Imidazole-1-propanamine → HCID 69481997, compound

HRID 2364396Notes

Reaction equation

HRID 2364396 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][N:14]1[C:23]2[C:18](=[N:19][CH:20]=[C:21]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[CH:22]=2)[C:17]([OH:32])=[C:16]([C:33](OCC)=[O:34])[C:15]1=[O:38].[N:39]1([CH2:44][CH2:45][CH2:46][NH2:47])[CH:43]=[CH:42][N:41]=[CH:40]1>CCO>[O:11]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2](=[O:1])[N:3]1[CH2:12][CH2:13][N:14]1[C:23]2[C:18](=[N:19][CH:20]=[C:21]([CH2:24][C:25]3[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=3)[CH:22]=2)[C:17]([OH:32])=[C:16]([C:33]([NH:47][CH2:46][CH2:45][CH2:44][N:39]2[CH:43]=[CH:42][N:41]=[CH:40]2)=[O:34])[C:15]1=[O:38]

Participants

4

Reactant 2

HCID 787361H-Imidazole-1-propanamineHCID 69480967ethyl 1-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 69481997HCID 69481997, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 1-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (0.025 g, 0.049 mmol) in EtOH (1 mL) under nitrogen was treated with 3-(1H-imidazol-1-yl)-1-propanamine (0.0072 mL, 0.061 mmol) for 30 min.@150° C. The reaction was further microwaved for 30 min.@150° C. after the addition of an additional equivalent (0.0072 mL) of the amine, cooled to ambient temperature, and the resulting suspension was filtered, washed with EtOH and then thoroughly dried under high vacuum to provide the title compound as a white solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.74-1.84 (m, 2 H), 3.18 (q, J=6.60 Hz, 2 H), 3.83 (t, J=6.95 Hz, 2 H), 3.91 (t, J=5.48 Hz, 2 H), 4.14 (s, 2 H), 4.57 (t, J=5.55 Hz, 2 H), 6.90 (t, J=1.05 Hz, 1 H) 7.09-7.18 (m, 3 H), 7.37 (td, J=6.00, 2.32 Hz, 2 H), 7.57 (t, J=1.12 Hz, 1 H), 7.70-7.75 (m, 2 H), 7.78-7.83 (m, 2 H), 8.19 (s, 1 H), 8.54 (s, 1 H), 9.93 (t, J=6.04 Hz, 1 H), 17.12 (bs, 1 H); ES+ MS: 595 (M+H+).

Workup

  1. customThe reaction was further microwaved for 30 min.@150° C.
  2. filtrationthe resulting suspension was filtered
  3. washwashed with EtOH
  4. customthoroughly dried under high vacuum

Sources & evidence

ORD record
ord-2d33105410a74cdba9e6b879a21d1fb2
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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