2-Aminopropanol → HCID 69482584, compound

HRID 2364486Notes

Reaction equation

HRID 2364486 reaction equation
[C:1]([N:4]([CH3:32])[CH2:5][CH2:6][N:7]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH:15]=2)[C:10]([OH:25])=[C:9]([C:26](OCC)=[O:27])[C:8]1=[O:31])(=[O:3])[CH3:2].[NH2:33][CH:34]([CH3:37])[CH2:35][OH:36]>CCO>[C:1]([N:4]([CH3:32])[CH2:5][CH2:6][N:7]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH:15]=2)[C:10]([OH:25])=[C:9]([C:26]([NH:33][CH:34]([CH3:37])[CH2:35][OH:36])=[O:27])[C:8]1=[O:31])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 51262-AminopropanolHCID 69481486HCID 69481486, compound

Product 1

HCID 69482584HCID 69482584, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 1-{2-[acetyl(methyl)amino]ethyl}-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (0.019 g, 0.039 mmol) in EtOH (3 mL) under nitrogen was treated with 2-amino-1-propanol (0.02 mL, 0.27 mmol) for 30 min. (160° C. in a microwave vessel. After the reaction was cooled to ambient temperature the resulting suspension was concentrated in vacuo, triturated with Et2O:MeOH, filtered, and the filtered solid was washed with Et2O then thoroughly dried under high vacuum to provide the title compound as an off-white solid: 1H NMR (400 MHz, DMSO-d6 (90° C.) δ ppm 1.23 (d, J=6.86 Hz, 3 H), 1.85 (s, 3 H), 2.95 (s, 3 H), 3.50-3.55 (m, 4 H), 4.08-4.11 (m, 1 H), 4.18 (s, 2 H), 4.35 (s, 2 H), 4.69-4.72 (m, 1 H), 7.10-7.15 (m, 2 H), 7.37-7.42 (m, 2 H), 8.08 (s, 1 H), 8.55 (s, 1 H), 10.29 (d, J=4.53 Hz, 1 H), 17.15 (s, 1 H); ES+ MS: 471 (M+H+).

Workup

  1. concentrationwas concentrated in vacuo
  2. customtriturated with Et2O
  3. filtrationMeOH, filtered
  4. washthe filtered solid was washed with Et2O
  5. customthen thoroughly dried under high vacuum

Sources & evidence

ORD record
ord-978e8e2369e74101816477c8d09b1883
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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