Ethanolamine → HCID 86612788, compound

HRID 2364454Notes

Reaction equation

HRID 2364454 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:40])=[C:14]([C:35](OCC)=[O:36])[C:15](=[O:34])[N:16]3[CH2:19][CH2:20][CH2:21][N:22]([CH3:33])[C:23]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[NH2:41][CH2:42][CH2:43][OH:44]>CCO>[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:40])=[C:14]([C:35]([NH:41][CH2:42][CH2:43][OH:44])=[O:36])[C:15](=[O:34])[N:16]3[CH2:19][CH2:20][CH2:21][N:22]([CH3:33])[C:23](=[O:24])[O:25][CH2:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 700Ethanolamine2×HCID 69479908HCID 69479908, compound

Product 1

HCID 86612788HCID 86612788, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-[3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)propyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (20 mg, 0.036 mmol) and 2-aminoethanol (13 μL, 0.22 mmol) were combined in EtOH (2 mL) and heated for 15 min. at 125° C. in a microwave vessel. Additional 2-aminoethanol (50 μL, 0.84 mmol) was added and the reaction was heated at 150° C. for 20 min. The mixture was evaporated in vacuo and partitioned between CH2Cl2 and 1N NaHSO4. After separating the layers, the aqueous phase was back-extracted with CH2Cl2. 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 10.37 (1H, b), 8.54 (1H, s), 7.93-8.03 (1H, m), 7.17-7.40 (7H, m), 7.11 (2H, t, J=9 Hz), 4.89-5.09 (3H, m), 4.12-4.22 (4H, m), 3.52-3.58 (2H, m), 3.40-3.45 (2H, m), 3.29 (3H, s), 2.81-2.88 (2H, m), 1.78 (b, 2H); ES+ MS: 563 (M+H+).

Workup

  1. temperaturethe reaction was heated at 150° C. for 20 min
  2. customThe mixture was evaporated in vacuo
  3. custompartitioned between CH2Cl2 and 1N NaHSO4
  4. customAfter separating the layers
  5. extractionthe aqueous phase was back-extracted with CH2Cl2
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customtriturated with Et2O

Sources & evidence

ORD record
ord-68b95197d63744c5b8de2936ed3a9695
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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