2-Morpholinoethylamine → HCID 69482009, compound

HRID 2364224Notes

Reaction equation

HRID 2364224 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:34])=[C:14]([C:29](OCC)=[O:30])[C:15](=[O:28])[N:16]3[CH2:19][C:20](=[O:27])[N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[NH2:35][CH2:36][CH2:37][N:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1>>[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:34])=[C:14]([C:29]([NH:35][CH2:36][CH2:37][N:38]4[CH2:43][CH2:42][O:41][CH2:40][CH2:39]4)=[O:30])[C:15](=[O:28])[N:16]3[CH2:19][C:20](=[O:27])[N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 4082852-MorpholinoethylamineHCID 69480365HCID 69480365, compound

Product 1

HCID 69482009HCID 69482009, compound

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[2-oxo-2-(1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate and 4-(2-aminoethyl)morpholine 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 light yellow rigid foam: 1H NMR (CDCl3) δ 10.41 (1H, m), 8.57 (1H, s), 7.15 (2H, dd, J=8.5, 6 Hz), 7.03 (3H, m), 4.92 (2H, s), 4.12 (2H, s), 3.99 (4H, m), 3.89 (2H, q, J=6 Hz), 3.72 (2H, m), 3.50 (2H, m), 3.46 (2H, m), 3.35 (2H, t, J=6 Hz), 2.93 (2H, br), 1.70 (2H, m), 1.61 (2H, m), 1.53 (2H, m); HRMS calcd for C29H34FN5O5+H+: 552.2622. Found: 552.2618 .

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 light yellow rigid foam

Sources & evidence

ORD record
ord-ce4c87e2f0e24e489f087c82e3535c2b
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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