1-Hydroxybenzotriazole → HCID 178505181, Verbindung

HRID 2237627

Reaktionsgleichung

Reaktionsgleichung von HRID 2237627
[NH2:1][C:2]1[C:7]2[C:8](=[O:29])[N:9]([C:13]3[CH:18]=[CH:17][C:16]([C@H:19]4[CH2:24][CH2:23][C@H:22]([CH2:25][C:26]([OH:28])=O)[CH2:21][CH2:20]4)=[CH:15][CH:14]=3)[CH2:10][CH2:11][O:12][C:6]=2[N:5]=[CH:4][N:3]=1.C[NH:31][SH:32](=[O:34])=[O:33].[CH:35]1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CCOC(C)=O>[NH2:1][C:2]1[C:7]2[C:8](=[O:29])[N:9]([C:13]3[CH:18]=[CH:17][C:16]([C@H:19]4[CH2:24][CH2:23][C@H:22]([CH2:25][C:26]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])=[O:28])[CH2:21][CH2:20]4)=[CH:15][CH:14]=3)[CH2:10][CH2:11][O:12][C:6]=2[N:5]=[CH:4][N:3]=1

Komponenten

6

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178486264HCID 178486264, VerbindungHCID 178508633HCID 178508633, Verbindung

Produkt 1

HCID 178505181HCID 178505181, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of {trans-4-[4-(4-amino-5-oxo-7,8-dihydropyrimido[5,4-f][1,4]oxazepin-6(5H)-yl)phenyl]cyclohexyl}acetic acid (50 mg, 0.13 mmol), from Example 2, N-methylsulfonamide (30 mg, 0.32 mmol) were added HOBT (29 mg, 0.19 mmol), EDCl (30 mg, 0.32 mmol) and TEA (19.1 mg, 0.19 mmol). After 18 hours, the reaction mixture was diluted into EtOAc, washed with water, dried over sodium sulfate and concentrated in vacuo. Reverse-phase chromatography afforded the desired product as a white solid, 5.3 mg. 1H NMR (400 MHz, DMSO-d6): δ 8.17 (s, 1H), 7.64 (br s, 2H) 7.20 (s, 4H), 4.58 (m, 2H), 3.92 (m, 2H), 3.20 (s, 3H), 2.42 (m, 1H), 2.17 (m, 2H), 1.73 (m, 5H), 1.40 (m, 2H), 1.05 m, 2H). m/z=474.4 (M+1). IC50 44.5 nM (range 34.2-75.0 nM).

Aufarbeitung

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-19d5230fcd6f46449a40fcd54ed26180
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07718645B2

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