4-Methylmorpholine → [(Z)-[amino-[5-chloro-1-(4-methylphenyl)sulfonyl-2-(1-methylpyrazol-4-yl)pyrrolo[2,3-b]pyridin-4-yl]methylidene]amino] 1-hydroxycyclobutane-1-carboxylate

HRID 2362739Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2362739
[Cl:1][C:2]1[CH:7]=[N:6][C:5]2[N:8]([S:17]([C:20]3[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)=[CH:10][C:4]=2[C:3]=1/[C:27](=[N:29]/[OH:30])/[NH2:28].[OH:31][C:32]1([C:36](O)=[O:37])[CH2:35][CH2:34][CH2:33]1.O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[N:6][C:5]2[N:8]([S:17]([C:20]3[CH:21]=[CH:22][C:23]([CH3:24])=[CH:25][CH:26]=3)(=[O:19])=[O:18])[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)=[CH:10][C:4]=2[C:3]=1/[C:27](=[N:29]/[O:30][C:36]([C:32]1([OH:31])[CH2:35][CH2:34][CH2:33]1)=[O:37])/[NH2:28]

Komponenten

8

Edukt 5

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 109534701-Hydroxycyclobutanecarboxylic acidHCID 1363794975-chloro-N'-hydroxy-1-(4-methylphenyl)sulfonyl-2-(1-methylpyrazol-4-yl)pyrrolo[2,3-b]pyridine-4-carboximidamide

Produkt 1

HCID 87233275[(Z)-[amino-[5-chloro-1-(4-methylphenyl)sulfonyl-2-(1-methylpyrazol-4-yl)pyrrolo[2,3-b]pyridin-4-yl]methylidene]amino] 1-hydroxycyclobutane-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of (Z)-5-chloro-N′-hydroxy-2-(1-methyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine-4-carboximidamide (Example 138B) (44 mg, 0.099 mmol), 1-hydroxycyclobutanecarboxylic acid (12.63 mg, 0.109 mmol), 1-hydroxybenzotriazole hydrate (7.57 mg, 0.049 mmol), and 4-methylmorpholine (0.038 mL, 0.346 mmol) in anhydrous dimethylformamide (1 mL) was treated with N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (28.4 mg, 0.148 mmol). The reaction was stirred for 3 hours at ambient temperature. The reaction was diluted with ethyl acetate and washed with water and brine. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated to provide the title compound. MS ESI(+) m/z 542.9 [M+H]+.

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-17df7cbb8c264c6bb57ca48254ee4519
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08691810B2

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