(S)-(+)-1-Aminopropan-2-ol → HCID 69480974, compound

HRID 2364338Notes

Reaction equation

HRID 2364338 reaction equation
[CH3:1][N:2]([CH3:31])[C:3](=[O:30])[CH2:4][N:5]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH:13]=2)[C:8]([OH:23])=[C:7]([C:24](OCC)=[O:25])[C:6]1=[O:29].[NH2:32][CH2:33][C@@H:34]([OH:36])[CH3:35]>>[CH3:1][N:2]([CH3:31])[C:3](=[O:30])[CH2:4][N:5]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([CH2:15][C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[CH:13]=2)[C:8]([OH:23])=[C:7]([C:24]([NH:32][CH2:33][C@@H:34]([OH:36])[CH3:35])=[O:25])[C:6]1=[O:29]

Participants

3

Reactant 2

HCID 7311736(S)-(+)-1-Aminopropan-2-olHCID 58882926HCID 58882926, compound

Product 1

HCID 69480974HCID 69480974, compound

Procedure

This compound was prepared from ethyl 1-[2-(dimethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo -1,2-dihydro-1,5-naphthyridine-3-carboxylate and (2S)-1-amino-2-propanol employing methods similar to those described in Example 245 and was purified by reverse phase preparative HPLC (C-18 stationary phase; 10-100% CH3CN/water/0.1% formic acid mobile phase). The product was obtained as a white solid: 1H NMR (d6-DMSO) δ 10.28 (1H, t, J=5 Hz), 8.50 (1H, s), 7.75 (1H, s), 7.31 (2H, m), 7.12 (2H, m), 5.12 (2H, m), 4.94 (1H, d, J=5 Hz), 4.11 (2H, s), 3.78 (1H, m), 3.40 (1H, m), 3.18 (1H, m), 3.12 (3H, s), 2.82 (3H, s), 1.07 (3H, d, J=6 Hz); HRMS calcd for C23H25FN4O5+H+: 457.18817. Found: 457.18875.

Workup

  1. customwas purified by reverse phase preparative HPLC (C-18 stationary phase; 10-100% CH3CN/water/0.1% formic acid mobile phase)
  2. customThe product was obtained as a white solid

Sources & evidence

ORD record
ord-d48249ed1e144064b09fbf9c90958760
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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