Diglycolamine → HCID 69482533, compound

HRID 2364475Notes

Reaction equation

HRID 2364475 reaction equation
[F:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][C:7]2[CH:16]=[C:15]3[C:10]([C:11]([OH:31])=[C:12]([C:26](OCC)=[O:27])[C:13](=[O:25])[N:14]3[CH2:17][CH2:18][N:19]3[CH2:23][CH2:22][CH2:21][C:20]3=[O:24])=[N:9][CH:8]=2)=[CH:4][CH:3]=1.[NH2:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][OH:40]>CCO>[F:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][C:7]2[CH:16]=[C:15]3[C:10]([C:11]([OH:31])=[C:12]([C:26]([NH:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][OH:40])=[O:27])[C:13](=[O:25])[N:14]3[CH2:17][CH2:18][N:19]3[CH2:23][CH2:22][CH2:21][C:20]3=[O:24])=[N:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 13578DiglycolamineHCID 58882907Ethyl 7-(4-fluorobenzyl)-4-hydroxy-2-oxo-1-[2-oxopyrrolidin-1-yl ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 69482533HCID 69482533, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 7-(4-fluorobenzyl)-4-hydroxy-2-oxo-1-[2-(2-oxopyrrolidin-1-yl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate (30 mg, 0.066 mmol) and 2-[(2-aminoethyl)oxy]ethanol (100 μL) was heated in EtOH (3 mL) at 175° C. for 45 min. in a microwave. The reaction mixture was evaporated in vacuo and partitioned between 1N NaHSO4 and CH2Cl2. The aqueous phase was back-extracted with CH2Cl2 and the combined organic layers were dried over MgSO4, filtered, evaporated in vacuo and triturated with Et2O to provide the product as a white solid: 1H NMR (d6-DMSO) δ 10.35 (1H, t, J=5 Hz), 8.54 (1H, s), 8.09 (1H, s), 7.39 (2H, dd, J=5, 9 Hz), 7.11 (2H, t, J=9 Hz), 4.59 (1H, t, J=5 Hz), 4.36 (2H, t, J=6 Hz), 4.14 (2H, s), 3.33-3.56 (12H, m), 1.93 (2H, t, J=8 Hz), 1.74 (2H, t, J=7 Hz); ES+ MS: 513 (M+H+).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. custompartitioned between 1N NaHSO4 and CH2Cl2
  3. extractionThe aqueous phase was back-extracted with CH2Cl2
  4. dry with materialthe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customtriturated with Et2O

Sources & evidence

ORD record
ord-c38f9cd21d3943cdb0721ae06f289a65
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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