1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → Tert-butyl 3-[(2-{[(3,5-bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-benzoyl)-ethyl-amino]-propionate

HRID 604062Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 604062
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[CH2:6][N:7]([CH2:15][C:16]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21]C=1C(O)=O)[C:8]1[N:13]=[CH:12][C:11]([Br:14])=[CH:10][N:9]=1.[CH2:38]([NH:40][CH2:41][CH2:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH3:39].[OH2:50].O.ON1[C:57]2C=CC=C[C:56]=2N=N1.Cl.C(N=C=NCCCN(C)C)C>O1CCCC1.C(OCC)(=O)C.O.C(N(CC)CC)C>[F:37][C:2]([F:1])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[CH2:6][N:7]([CH2:15][C:16]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:39]=1[C:38]([N:40]([CH2:56][CH3:57])[CH2:41][CH2:42][C:43]([O:45][C:46]([CH3:48])([CH3:47])[CH3:49])=[O:44])=[O:50])[C:8]1[N:13]=[CH:12][C:11]([Br:14])=[CH:10][N:9]=1

Komponenten

9

Edukt 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 20566209Tert-butyl 3-(ethylamino)propanoateHCID 666034961-Hydroxybenzotriazole dihydrateHCID 86626801HCID 86626801, Verbindung

Produkt 1

HCID 86626819Tert-butyl 3-[(2-{[(3,5-bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-benzoyl)-ethyl-amino]-propionateAusbeute 98,6 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-{[(3,5-Bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-benzoic acid (250 mg) is dissolved in tetrahydrofuran (5 ml), and thereto are added tert-butyl 3-ethylamino-propionate (103 mg), 1-hydroxybenzotriazole dihydrate (81 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (114 mg) and triethylamine (83 μl), and the mixture is stirred at room temperature overnight. To the reaction solution are added water and ethyl acetate, and the mixture is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=19:1→4:1) to give tert-butyl 3-[(2-{[(3,5-bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-benzoyl)-ethyl-amino]-propionate (310 mg). MS (m/z): 757/759 [M+H]+

Aufarbeitung

  1. customthe mixture is separated
  2. washthe organic layer is washed with a saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=19:1→4:1)

Quellen und Nachweise

ORD-Eintrag
ord-e766a74ffd3b464fb001bf275318aac2
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906517B2

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