(R)-(-)-2-Amino-1-propanol → HCID 69480464, compound

HRID 2364534Notes

Reaction equation

HRID 2364534 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][C@H:34]([CH3:37])[CH2:35][OH:36]>>[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][C@H:34]([CH3:37])[CH2:35][OH:36])=[O:27])[C:8]1=[O:31])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 80308(R)-(-)-2-Amino-1-propanolHCID 69481486HCID 69481486, compound

Product 1

HCID 69480464HCID 69480464, compound

Procedure

This compound was prepared from ethyl 1-{2-[acetyl(methyl)amino]ethyl}-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and (2R)-2-amino-1-propanol using methods similar to Example 574: step 2 to provide an off-white solid: 1H NMR (400 MHz, DMSO-d6@90° C.) δ ppm 1.23 (d, J=6.72 Hz, 3 H), 1.85 (s, 3 H), 2.80 (s, 1 H), 2.95 (s, 2 H), 3.50-3.55 (m, 4 H), 4.05-4.14 (m, 1 H), 4.18 (d, J=0.82 Hz, 2 H), 4.35 (s, 2 H), 4.70 (t, J=5.56 Hz, 1 H), 7.09-7.15 (m, 2 H), 7.36-7.42 (m, 2 H), 8.08 (s, 1 H), 8.55 (s, 1 H), 10.06-10.42 (m, 1 H), 17.06-17.18 (m, 1 H); ES− MS: 471 (M+H+).

Workup

  1. customto provide an off-white solid

Sources & evidence

ORD record
ord-86d002b72dbb4d038f46c8bf421093f0
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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