(2R)-1-aminopropan-2-ol → HCID 69481003, compound

HRID 2364512Notes

Reaction equation

HRID 2364512 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][CH2:34][C@H:35]([OH:37])[CH3:36]>>[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:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=3)[CH:15]=2)[C:10]([OH:25])=[C:9]([C:26]([NH:33][CH2:34][C@H:35]([OH:37])[CH3:36])=[O:27])[C:8]1=[O:31])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 439938(2R)-1-aminopropan-2-olHCID 69481486HCID 69481486, compound

Product 1

HCID 69481003HCID 69481003, 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)-1-amino-2-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 1.14 (d, J=6.17 Hz, 3 H), 1.84 (s, 3 H), 2.91-2.98 (m, 3 H), 3.23-3.33 (m, 1 H), 3.40-3.50 (m, 1 H), 3.54 (t, J=6.72 Hz, 2 H), 3.85-3.88 (m, 1 H), 4.18 (s, 2 H), 4.37 (d, J=7.55 Hz, 2 H), 4.65 (d, J=5.90 Hz, 1 H), 7.12 (t, J=8.51 Hz, 2 H), 7.36-7.43 (m, 2 H), 8.07 (s, 1 H), 8.55 (s, 1 H), 10.35 (s, 1 H), 16.97-17.20 (m, 1 H); ES+ MS: 471 (M+H+).

Workup

  1. customto provide an off-white solid

Sources & evidence

ORD record
ord-7c71bcedfb7145f9af4a80f0099e5bf3
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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