Ethylenediamine → HCID 86610611, compound

HRID 506378Notes

Reaction equation

HRID 506378 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[N:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=2)[C@@H:9]([NH:18][C:19]2[C:24]([CH2:25][C:26]3[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[C:28]([C:36]([F:39])([F:38])[F:37])[CH:27]=3)=[CH:23][C:22]([C:40](OCC)=[NH:41])=[CH:21][N:20]=2)[CH2:8][C@H:7]1[CH2:45][CH3:46])=[O:5])[CH3:2].[CH2:47](N)[CH2:48][NH2:49].C(OCC)(=O)C>C(O)C.[Cl-].[Na+].O>[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[N:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=2)[C@@H:9]([NH:18][C:19]2[C:24]([CH2:25][C:26]3[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[C:28]([C:36]([F:39])([F:38])[F:37])[CH:27]=3)=[CH:23][C:22]([C:40]3[NH:49][CH2:48][CH2:47][N:41]=3)=[CH:21][N:20]=2)[CH2:8][C@H:7]1[CH2:45][CH3:46])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 3301EthylenediamineHCID 8857Ethyl AcetateHCID 86610609HCID 86610609, compound

Product 1

HCID 86610611HCID 86610611, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

(2R*,4S*)-4-{[3,5-Bis(trifluoromethyl)benzyl]-(5-ethoxycarbonimidoylpyridin-2-yl)}amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (100 mg) and ethylenediamine (150 μl) are dissolved in ethanol (3 ml), and the mixture is stirred under reflux for 4 hours. After cooling to room temperature, a saturated brine and ethyl acetate are added to the reaction solution. The organic layer is dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by column chromatography (NH-silica gel; hexane: ethyl acetate=1:1→1:2) to give (2R*,4S*)-4-{[3,5-bis(trifluoromethyl)benzyl]-[5-(4,5-dihydro-1H-imidazol-2-yl)pyridin-2-yl]}amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (96 mg). MS (m/z): 651 [M+H]+

Workup

  1. temperatureunder reflux for 4 hours
  2. dry with materialThe organic layer is dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue is purified by column chromatography (NH-silica gel; hexane: ethyl acetate=1:1→1:2)

Sources & evidence

ORD record
ord-2c6f6b451acc4dc5a98ad944e189fa32
Source dataset
uspto-grants-2010_08
Patent number
US07781443B2

Reaction notes

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