1-Hydroxybenzotriazole → rac-{1-[({7-[(2-Chloro-6-fluorobenzyl)oxy]-2,5-dimethylpyrazolo[1,5-a]pyridin-3-yl}carbonyl)amino]-2-methylpentan-2-yl}carbamic Acid tert-butyl Ester

HRID 1486304Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1486304
[Cl:1][C:2]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:3]=1[CH2:4][O:5][C:6]1[N:11]2[N:12]=[C:13]([CH3:18])[C:14]([C:15](O)=[O:16])=[C:10]2[CH:9]=[C:8]([CH3:19])[CH:7]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[C:47]([O:51][C:52](=[O:61])[NH:53][C:54]([CH2:59][NH2:60])([CH3:58])[CH2:55][CH2:56][CH3:57])([CH3:50])([CH3:49])[CH3:48].C(N(CC)C(C)C)(C)C>O1CCCC1>[C:47]([O:51][C:52](=[O:61])[NH:53][C:54]([CH3:58])([CH2:55][CH2:56][CH3:57])[CH2:59][NH:60][C:15]([C:14]1[C:13]([CH3:18])=[N:12][N:11]2[C:6]([O:5][CH2:4][C:3]3[C:20]([F:24])=[CH:21][CH:22]=[CH:23][C:2]=3[Cl:1])=[CH:7][C:8]([CH3:19])=[CH:9][C:10]=12)=[O:16])([CH3:48])([CH3:49])[CH3:50]

Komponenten

7

Edukt 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 84723920rac-tert-Butyl (1-amino-2-methylpentan-2-yl)carbamateHCID 1178595577-(2-Chloro-6-fluorobenzyloxy)-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylic Acid

Produkt 1

HCID 117864595rac-{1-[({7-[(2-Chloro-6-fluorobenzyl)oxy]-2,5-dimethylpyrazolo[1,5-a]pyridin-3-yl}carbonyl)amino]-2-methylpentan-2-yl}carbamic Acid tert-butyl EsterAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 26 mg (0.074 mmol) of 7-(2-chloro-6-fluorobenzyloxy)-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylic acid (Example 137A) in 3 ml of tetrahydrofuran was admixed with 17 mg (0.09 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 14 mg (0.09 mmol) of 1-hydroxybenzotriazole, 21 mg (0.096 mmol) of rac-(1-aminomethyl-1-methylbutyl)carbamic acid tert-butyl ester from Example 152A and 0.039 ml (0.222 mmol) of N,N-diisopropylethylamine. The mixture was stirred at room temperature for a further 18 hours. The reaction mixture was then heated to 60° C. for 3 hours. After concentration under reduced pressure, the residue was partitioned between dichloromethane and water. The organic phase was removed and concentrated under reduced pressure, which gave 40 mg (99% yield) of the target compound.

Aufarbeitung

  1. temperatureThe reaction mixture was then heated to 60° C. for 3 hours
  2. concentrationAfter concentration under reduced pressure
  3. customthe residue was partitioned between dichloromethane and water
  4. customThe organic phase was removed
  5. concentrationconcentrated under reduced pressure, which

Quellen und Nachweise

ORD-Eintrag
ord-c8c2640b235d41d3841a2223a691b67e
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09422285B2

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