1-Amino-2-propanol → HCID 69481016, compound

HRID 2364252Notes

Reaction equation

HRID 2364252 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:33])=[C:14]([C:28](OCC)=[O:29])[C:15](=[O:27])[N:16]3[CH2:19][C:20](=[O:26])[N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[NH2:34][CH2:35][CH:36]([OH:38])[CH3:37]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:33])=[C:14]([C:28]([NH:34][CH2:35][CH:36]([OH:38])[CH3:37])=[O:29])[C:15](=[O:27])[N:16]3[CH2:19][C:20](=[O:26])[N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[N:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 41-Amino-2-propanolHCID 58882934HCID 58882934, compound

Product 1

HCID 69481016HCID 69481016, compound

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[2-oxo-2-(1-pyrrolidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate and (±)-1-amino-2-propanol employing methods similar to those those described in Example 9 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 (CDCl3) δ 14.5 (1H, br), 10.32 (1H, m), 8.54 (1H, s), 7.15 (2H, dd, J=8.5, 5.5 Hz), 7.08 (1H, s), 7.02 (2H, t, J=8.5 Hz), 4.88 (2H, m), 4.11 (2H, s), 4.05 (1H, m), 3.61 (1H, m), 3.51-3.44 (4H, m), 3.35 (1H, m), 2.20 (1H, d, J=4 Hz), 2.04 (2H, m, J=7 Hz), 1.89 (2H, m, J=7 Hz), 1.26 (3H, d, J=6 Hz); HRMS calcd for C25H27FN4O5+H+: 483.2044. Found: 483.2029.

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-35fc3c1510614ced8799ab82e3670e83
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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