Cyclopropanemethanamine, N-propyl- → 7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridine-3-carboxylic acid cyclopropylmethylpropylamide

HRID 2416114

Reaktionsgleichung

Reaktionsgleichung von HRID 2416114
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[N:10]1[CH2:15][CH2:14][CH2:13][C:12]2=[C:16]([C:20]([OH:22])=O)[N:17]([CH3:19])[N:18]=[C:11]12.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[CH2:46]([NH:49][CH2:50][CH:51]1[CH2:53][CH2:52]1)[CH2:47][CH3:48]>ClCCl.C(N(CC)CC)C>[CH:51]1([CH2:50][N:49]([CH2:46][CH2:47][CH3:48])[C:20]([C:16]2[N:17]([CH3:19])[N:18]=[C:11]3[C:12]=2[CH2:13][CH2:14][CH2:15][N:10]3[C:3]2[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=2[Cl:1])=[O:22])[CH2:53][CH2:52]1

Komponenten

7

Edukt 4

HCID 117787Cyclopropanemethanamine, N-propyl-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 221362637-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridine-3-carboxylic acid

Produkt 1

HCID 221362777-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridine-3-carboxylic acid cyclopropylmethylpropylamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

7-(2-Chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridine-3-carboxylic acid (107.0 mg), 1-hydroxybenzotriazole hydrate (50.3 mg), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (72.5 mg), triethylamine (93 μL), and N-propylcyclopropanemethylamine (49 μL) were combined in 4 mL of dichloromethane and stirred at room temperature over night. The reaction mixture was then partitioned between ethyl acetate and 1M hydrochloric acid. The ethyl acetate solution was washed with aqueous sodium bicarbonate, dried with magnesium sulfate, and concentrated. The crude product was chromatographed on silica gel eluting with an acetone/hexane gradient giving a solid. Recrystallization from hexane provided 75.6 mg of 7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridine-3-carboxylic acid cyclopropylmethylpropylamide, mp 120.6-122.0° C.

Aufarbeitung

  1. customThe reaction mixture was then partitioned between ethyl acetate and 1M hydrochloric acid
  2. washThe ethyl acetate solution was washed with aqueous sodium bicarbonate
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated
  5. customThe crude product was chromatographed on silica gel eluting with an acetone/hexane gradient
  6. customgiving a solid
  7. customRecrystallization from hexane

Quellen und Nachweise

ORD-Eintrag
ord-d281ab1f985b48288ba991646dad468f
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06821984B2

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