Triethylamine → 6-(2-(9H-fluoren-9-ylidene)acetamido)-N-(2-amino-4-methylphenyl)hexanamide

HRID 1926195

Reaktionsgleichung

Reaktionsgleichung von HRID 1926195
[CH:1]1[C:13]2[C:12](=[CH:14][C:15]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23](O)=[O:24])=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl.C(N=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.[CH3:55][C:56]1[CH:61]=[CH:60][C:59]([NH2:62])=[C:58]([NH2:63])[CH:57]=1>[Cl-].[Na+].O.CN(C=O)C>[CH:10]1[C:11]2[C:12](=[CH:14][C:15]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([NH:62][C:59]3[CH:60]=[CH:61][C:56]([CH3:55])=[CH:57][C:58]=3[NH2:63])=[O:24])=[O:16])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 103323,4-DiaminotolueneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57495416HCID 57495416, VerbindungHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 445403416-(2-(9H-fluoren-9-ylidene)acetamido)-N-(2-amino-4-methylphenyl)hexanamideAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

6-(2-(9H-fluoren-9-ylidene)acetamido)hexanoic acid (335 mg, 1 mmol), and 8 ml of DMF were stirred at room temperature while 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (394 mg, 2 mmol), hydroxy-benzotriazole (162 mg, 1.2 mmol), triethylamine (404 mg, 4 mmol) and 4-methyl-o-phenylenediamine (146 mg, 1.2 mmol) were added. The mixture was stirred for 24 hours at room temperature. The mixture was diluted with 400 mL of brine. The solids were collected by vacuum filtration, washed with water and dried under vacuum to give the title compound (369 mg, 84% yield) as a brown solid. 1H NMR (DMSO-d6) δ1.39 (m, 2H, CH2), 1.57 (m, 2H, CH2), 1.63 (m, 2H, CH2), 2.11 (s, 3H, CH3), 2.31 (t, J=8.0 Hz, 2H, CH2CO), 3.27 (m, 2H, NCH2), 4.72 (s, 2H, benzene-NH2), 6.31 (d, J=8.0 Hz, 1H, Ar—H), 6.61 (s, 1H, Ar—H), 6.99 (d, J=8.0 Hz, 1H, Ar—H), 7.08 (s, 1H, ═CH—CO), 7.33 (m, 2H, Ar—H), 7.40 (m, 2H, Ar—H), 7.76 (d, J=8.0 Hz, 1H, Ar—H), 7.82 (m, 2H, Ar—H), 8.53 (t, J=4.0 Hz, 1H, CONH), 8.69 (d, J=8.0 Hz, 1H, Ar—H), 9.08 (s, 1H, benzene-NH). LC-MS (m/z) 440 (M+1).

Aufarbeitung

  1. additionwere added
  2. filtrationThe solids were collected by vacuum filtration
  3. washwashed with water
  4. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-a3aa1803a68c452c88e05a805aabbab9
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178577B2

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