2-Morpholinoethylamine → HCID 58882892, compound

HRID 2364206Notes

Reaction equation

HRID 2364206 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][CH2:36][N:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]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:33])=[C:14]([C:28]([NH:34][CH2:35][CH2:36][N:37]4[CH2:42][CH2:41][O:40][CH2:39][CH2:38]4)=[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

Participants

3

Reactant 2

HCID 4082852-MorpholinoethylamineHCID 58882934HCID 58882934, compound

Product 1

HCID 58882892HCID 58882892, 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 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 white rigid foam: 1H NMR (CDCl3) δ 10.39 (1H, br m), 8.55 (1H, s), 7.15 (3H, m), 7.02 (2H, t, J=9 Hz), 4.85 (2H, s), 4.12 (2H, s), 3.98 (4H, br), 3.88 (2H, q, J=6 Hz), 3.72 (2H, br), 3.54 (2H, t, J=7 Hz), 3.45 (2H, t, J=7 Hz), 3.35 (2H, t, J=6 Hz), 2.92 (2H, br), 2.06 (2H, m, J=7 Hz), 1.90 (2H, m, J=7 Hz); HRMS calcd for C28H32FN5O5+H+: 538.2466. Found: 538.2460.

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 rigid foam

Sources & evidence

ORD record
ord-49fc80974ffe493ea060de473ed8c3c9
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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