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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 1826054
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인쇄 미리보기

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HRID 1826054 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 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

생성물 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)acrylamide수율 71%

시약·촉매·용매 1

HCID 31275
1,4-Dioxane
용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-7e4bf521eb1f4a8a80f91c575d85818f
출처 데이터셋
uspto-grants-2006_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07049310B2

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