1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-((1R)-6-(2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)-1,2,3,4-tetrahydronaphthalen-1-yl)-2-(3-oxo-1-tosylpiperazin-2-yl)acetamide

HRID 747059Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 747059
[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[C@H:19]([NH2:23])[CH2:18][CH2:17][CH2:16]3)[O:4][N:3]=1.[O:24]=[C:25]1[NH:30][CH2:29][CH2:28][N:27]([S:31]([C:34]2[CH:40]=[CH:39][C:37]([CH3:38])=[CH:36][CH:35]=2)(=[O:33])=[O:32])[CH:26]1[CH2:41][C:42](O)=[O:43].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[C@H:19]([NH:23][C:42](=[O:43])[CH2:41][CH:26]2[C:25](=[O:24])[NH:30][CH2:29][CH2:28][N:27]2[S:31]([C:34]2[CH:40]=[CH:39][C:37]([CH3:38])=[CH:36][CH:35]=2)(=[O:33])=[O:32])[CH2:18][CH2:17][CH2:16]3)[O:4][N:3]=1

Komponenten

7

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 620340531-[(4-methylphenyl)sulfonyl]-3-oxo-2-Piperazineacetic acidHCID 69078045(1R)-6-(2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)-1,2,3,4-tetrahydronaphthalen-1-amine

Produkt 1

HCID 11250383N-((1R)-6-(2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)-1,2,3,4-tetrahydronaphthalen-1-yl)-2-(3-oxo-1-tosylpiperazin-2-yl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a 100 mL round bottom flask was added (1R)-6-(2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)-1,2,3,4-tetrahydronaphthalen-1-amine (25.0 mg, 0.06 mmol), followed by 2-(3-oxo-1-tosylpiperazin-2-yl)acetic acid (50 mg, 0.016 mmol), dry CH2Cl2 (10 mL), HATU (12 mg, 0.03 mmol), EDCI (13 mg, 0.068 mmol) and hunig base (0.022 mL, 0.123 mmol). The resulting mixture was stirred at rt for 20 h. Removed solvent to dryness. Solvent was removed. The residue was purified by chromatography on silica gel. Elution with CH2Cl2:MeOH mixture (97:3) gave final compound. MS m/z: 600.3 (M+H). Calc'd. for C32H33N5O5S -599.71.s

Aufarbeitung

  1. customSolvent was removed
  2. customThe residue was purified by chromatography on silica gel
  3. washElution with CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-e794a0f63a3e44afa4605e71b2873f10
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07393852B2

Notizen zur Reaktion

Wird geladen…