Ethoxyethylamine → HCID 58882941, compound

HRID 2364203Notes

Reaction equation

HRID 2364203 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]([N:22]([CH3:27])[CH2:23][CH2:24][O:25][CH3:26])=[O:21])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[CH2:35]([O:37][CH2:38][CH2:39][NH2:40])[CH3:36]>>[CH2:35]([O:37][CH2:38][CH2:39][NH:40][C:29]([C:14]1[C:15](=[O:28])[N:16]([CH2:19][C:20]([N:22]([CH3:27])[CH2:23][CH2:24][O:25][CH3:26])=[O:21])[C:17]2[C:12]([C:13]=1[OH:34])=[N:11][CH:10]=[C:9]([CH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH:18]=2)=[O:30])[CH3:36]

Participants

3

Reactant 2

HCID 66970EthoxyethylamineHCID 58882985HCID 58882985, compound

Product 1

HCID 58882941HCID 58882941, compound

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-(2-{methyl[2-(methyloxy)ethyl]amino}-2-oxoethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and 2-ethoxyethylamine employing methods similar to 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 an off-white solid: 1H NMR (CDCl3) mixture of rotamers δ 10.20 (1H, br), 8.56 and 8.52 (1H, s), 7.38 and 7.10 (1H, s), 7.16-7.09 (2H, m), 7.04-6.98 (2H, m), 5.21 and 4.98 (2H, s), 4.11 (2H, s), 3.74-3.50 (10H, m), 3.34 and 3.32 (3H, s), 3.18 and 2.97 (3H, s), 1.22 and 1.23 (3H, t, J=7 Hz); HRMS calcd for C26H31FN4O6+H+: 515.2306. Found: 515.2293.

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 an off-white solid

Sources & evidence

ORD record
ord-cc9bde6c7b2744978de026f88a4afab7
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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