Hydrochloric Acid → (E)-N-(1-methyl-1H-indol-3-ylmethyl)-N-methyl-3-(6-amino-7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide

HRID 1826054Notes

Reaction equation

HRID 1826054 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][N:12]([CH3:42])[C:13](=[O:41])/[CH:14]=[CH:15]/[C:16]2[CH:17]=[N:18][C:19]3[NH:20][C:21](=[O:40])[CH:22]([N:26]=C(C4C=CC=CC=4)C4C=CC=CC=4)[CH2:23][C:24]=3[CH:25]=2)=[CH:3]1.Cl.[OH-].[Na+]>O1CCOCC1>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][N:12]([CH3:42])[C:13](=[O:41])/[CH:14]=[CH:15]/[C:16]2[CH:17]=[N:18][C:19]3[NH:20][C:21](=[O:40])[CH:22]([NH2:26])[CH2:23][C:24]=3[CH:25]=2)=[CH:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23574461(E)-N-(1-methyl-1H-indol-3-ylmethyl)-N-methyl-3-[6-(benzhydrylideneamino)-7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl]acrylamide

Product 1

HCID 10340289(E)-N-(1-methyl-1H-indol-3-ylmethyl)-N-methyl-3-(6-amino-7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamideYield 71%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of (E)-N-(1-methyl-1H-indol-3-ylmethyl)-N-methyl-3-[6-(benzhydrylideneamino)-7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl]acrylamide (0.5 g, 0.9 mmole) in dioxane (15 mL) was added 1 N HCl (10 mL) with stirring at RT. After approximately 5 min the suspension cleared up then gradually reformed. After stirring for 1 h the reaction was neutralized with 1 N NaOH (10 mL) and concentrated to near dryness under vacuum. The resulting suspension was diluted with H2O (20 mL) and filtered, and the solid was rinsed with cold H2O and dried under vacuum. The slightly pinkish solid was triturated with Et2O, filtered, and dried under vacuum to give the title compound (248 mg, 71%) as an off-white solid: MS (ES) m/e 390.4 (M+H)+.

Workup

  1. stirringAfter stirring for 1 h the reaction
  2. concentrationconcentrated
  3. additionThe resulting suspension was diluted with H2O (20 mL)
  4. filtrationfiltered
  5. washthe solid was rinsed with cold H2O
  6. customdried under vacuum
  7. customThe slightly pinkish solid was triturated with Et2O
  8. filtrationfiltered
  9. customdried under vacuum

Sources & evidence

ORD record
ord-7e4bf521eb1f4a8a80f91c575d85818f
Source dataset
uspto-grants-2006_05
Patent number
US07049310B2

Reaction notes

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