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Hexylamine → HCID 178444844, Verbindung

HRID 1898446
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1898446
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[NH:22][C:21]2[C:16]3[N:17]=[C:18]([CH3:20])[O:19][C:15]=3[C:14]([C:23]([OH:25])=O)=[CH:13][C:12]=2[N:11]=1.S(Cl)(Cl)=O.[CH2:30]([NH2:36])[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35].CCN(C(C)C)C(C)C>C1C=CC=CC=1.C1COCC1>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[NH:9][C:10]1[NH:22][C:21]2[C:16]3[N:17]=[C:18]([CH3:20])[O:19][C:15]=3[C:14]([C:23]([NH:36][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[O:25])=[CH:13][C:12]=2[N:11]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8102HexylamineHCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 178432356HCID 178432356, Verbindung

Produkt 1

HCID 178444844HCID 178444844, VerbindungAusbeute 32,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241
Benzene
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 7-[(2,6-dichlorophenyl)amino]-2-methyl-8H-imidazo[4,5-e][1,3]benzoxazole-4-carboxylic acid (Intermediate-55, 0.050 g, 0.132 mmol) in benzene (2 mL) was added thionyl chloride (1.5 mL) at 5-10° C. The reaction mass was refluxed for 3 h. To a solution of hexan-1-amine (0.020 g, 0.198 mmol) in THF (5.0 mL), DIPEA (0.086 g, 0.663 mmol) was added under N2-atmosphere at RT. The solution was stirred for 1 h at RT and above prepared solution was added to reaction mixture. The whole reaction mass was stirred at RT for 1 h. Thionyl chloride was removed under vacuum and stripped out with THF. The reaction mass was quenched in ice water and extracted with ethyl acetate. The organic layer was concentrated. The obtained product was further purified by column chromatography on neutral alumina eluting with 1.5-2.0% MeOH:DCM to afford 0.020 g of the desired product. 1HNMR (DMSO-d6): δ 0.83-0.85 (s, 3H), 1.26 (s, 6H), 1.51-1.54 (m, 2H), 2.61 (s, 3H), 3.30 (m, 2H), 7.30 (s, 1H), 7.57 (s, 3H), 7.90 (s, 1H), 9.30 (s, 1H), 11.40-11.50 (s, 1H); MS [M+H]+: 460.41

Aufarbeitung

  1. temperatureThe reaction mass was refluxed for 3 h
  2. customabove prepared solution
  3. additionwas added to reaction mixture
  4. stirringThe whole reaction mass was stirred at RT for 1 h
  5. customThionyl chloride was removed under vacuum
  6. customThe reaction mass was quenched in ice water
  7. extractionextracted with ethyl acetate
  8. concentrationThe organic layer was concentrated
  9. customThe obtained product was further purified by column chromatography on neutral alumina eluting with 1.5-2.0% MeOH

Quellen und Nachweise

ORD-Eintrag
ord-d2b39de9962540418c0f9ba721b394d3
Quelldatensatz
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08519149B2

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