4-Methylmorpholine → {1-[2-[2-Cyclopropylmethyl-4-(1-methylcarbamoyl-2-naphthalen-2-ylethyl)-piperazin-1-yl]-1-(4-fluorobenzyl)-2-oxo-ethylcarbamoyl]cyclopropyl}-carbamic acid tert-butyl ester

HRID 720174Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 720174
[NH2:1][CH:2]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=1)[C:3]([N:5]1[CH2:10][CH2:9][N:8]([CH:11]([CH2:16][C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=2)[C:12]([NH:14][CH3:15])=[O:13])[C:7](=O)[CH:6]1[CH2:28][CH:29]1[CH2:31][CH2:30]1)=[O:4].[C:40]([O:44][C:45]([NH:47][C:48]1([C:51]([OH:53])=O)[CH2:50][CH2:49]1)=[O:46])([CH3:43])([CH3:42])[CH3:41].ON1C2C=CC=CC=2N=N1.CN1CCOCC1.CN(C)CCCN=C=NCC>CN(C=O)C>[C:40]([O:44][C:45](=[O:46])[NH:47][C:48]1([C:51](=[O:53])[NH:1][CH:2]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)[C:3]([N:5]2[CH2:10][CH2:9][N:8]([CH:11]([C:12](=[O:13])[NH:14][CH3:15])[CH2:16][C:17]3[CH:26]=[CH:25][C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:18]=3)[CH2:7][CH:6]2[CH2:28][CH:29]2[CH2:31][CH2:30]2)=[O:4])[CH2:49][CH2:50]1)([CH3:41])([CH3:42])[CH3:43]

Komponenten

7

Edukt 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 6883961-((tert-Butoxycarbonyl)amino)cyclopropanecarboxylic acidHCID 102564532-[4-[2-amino-3-(4-fluorophenyl)-propionyl]-3-cyclopropylmethyl-2-oxo-piperazin-1-yl}-N-methyl-3-naphthalen-2-yl-propionamide

Produkt 1

HCID 69587840{1-[2-[2-Cyclopropylmethyl-4-(1-methylcarbamoyl-2-naphthalen-2-ylethyl)-piperazin-1-yl]-1-(4-fluorobenzyl)-2-oxo-ethylcarbamoyl]cyclopropyl}-carbamic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-{4-[2-amino-3-(4-fluorophenyl)-propionyl]-3-cyclopropylmethyl-2-oxo-piperazin-1-yl}-N-methyl-3-naphthalen-2-yl-propionamide, 18, (62 mg, 0.12 mmol) in DMF (2 mL) are added tert-butoxycarbonylamino-cyclopropanecarboxylic acid (28.5 mg, 0.14 mmol), 1-hydroxybenzotriazole (36 mg, 0.266 mmol), N-methylmorpholine (74 mg, 0.74 mmol) and 1-(3-dimethylamino-propyl)-3-ethylcarbodiimide (29 mg, 0.15 mmol) consecutively. The reaction mixture is stirred for 3 hours, quenched with aqueous NH4Cl and extracted several times with ethyl acetate. The combined extracts are dried over Na2SO4, filtered and concentrated in vacuo to a residue, which is purified over silica gel (CH2Cl2/CH3OH, 13:1) to afford the desired product.

Aufarbeitung

  1. customquenched with aqueous NH4Cl
  2. extractionextracted several times with ethyl acetate
  3. dry with materialThe combined extracts are dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a residue, which
  6. customis purified over silica gel (CH2Cl2/CH3OH, 13:1)

Quellen und Nachweise

ORD-Eintrag
ord-3f72ab637f3d4af7bd2779fd97224e9a
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07132539B2

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