1-Hydroxybenzotriazole → 3-Methyl-benzoic acid N'-(3-benzyloxy-7-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-2-carbonyl)-hydrazide

HRID 222619

Reaktionsgleichung

Reaktionsgleichung von HRID 222619
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]2[CH:16]=[C:17]([CH3:20])[CH:18]=[CH:19][C:12]2=[N:11][C:10]=1[C:21](O)=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24][C:25]1[CH:26]=[C:27]([CH:32]=[CH:33][CH:34]=1)[C:28]([NH:30][NH2:31])=[O:29].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>O1CCCC1>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]2[CH:16]=[C:17]([CH3:20])[CH:18]=[CH:19][C:12]2=[N:11][C:10]=1[C:21]([NH:31][NH:30][C:28](=[O:29])[C:27]1[CH:32]=[CH:33][CH:34]=[C:25]([CH3:24])[CH:26]=1)=[O:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 83082m-ToluohydrazideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 574945353-Benzyloxy-7-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-2-carboxylic acid

Produkt 1

HCID 593929153-Methyl-benzoic acid N'-(3-benzyloxy-7-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-2-carbonyl)-hydrazideAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of the product from Example 8.2 (200 mg, 0.644 mmol) in tetrahydrofuran (10 mL), was added 3-methylbenzoyl hydrazine (94.8 mg, 0.632 mmol), 1-hydroxybenzotriazole (6.98 mg, 0.0576 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (98 mg, 0.632 mmol) successively at room temperature. After 12 h the reaction solution was quenched with water (20 mL) and extracted with ethyl acetate. The extract was washed with 2N aqueous hydrochloric acid (20 mL), 2N aqueous sodium hydroxide (20 mL) dried (Na2SO4) and concentrated in vacuo to afford the desired compound (53%).

Aufarbeitung

  1. customAfter 12 h the reaction solution was quenched with water (20 mL)
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with 2N aqueous hydrochloric acid (20 mL), 2N aqueous sodium hydroxide (20 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2d0f32a8f28b413a84d23a18e050e97d
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207334B2

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