Triethylamine → HCID 57695422, Verbindung

HRID 1517356Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1517356
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:38])[N:7]([NH:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:8]([C@H:12]([NH:16][CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:30])[O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:13][C:14]#[CH:15])=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[F:46][C:47]1[C:55]([Cl:56])=[CH:54][CH:53]=[CH:52][C:48]=1[C:49](Cl)=[O:50]>ClCCl>[Cl:56][C:55]1[C:47]([F:46])=[C:48]([CH:52]=[CH:53][CH:54]=1)[C:49]([N:16]([CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:30])[O:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C@@H:12]([C:8]1[N:7]([NH:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:6](=[O:38])[C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]=1)[CH2:13][C:14]#[CH:15])=[O:50]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 27735983-Chloro-2-fluorobenzoyl chlorideHCID 57695471(R)-Benzyl 3-(1-(7-chloro-4-oxo-3-(phenylamino)-3,4-dihydroquinazolin-2-yl)but-3-ynylamino)propylcarbamate

Produkt 1

HCID 57695422HCID 57695422, VerbindungAusbeute 84,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

(R)-Benzyl 3-(1-(7-chloro-4-oxo-3-(phenylamino)-3,4-dihydroquinazolin-2-yl)but-3-ynylamino)propylcarbamate (0.28 g, 0.53 mmol) was dissolved in dichloromethane (5 mL). Triethylamine (0.22 mL, 1.60 mmol) was added followed by the addition of 2-fluoro-3-chlorobenzoyl chloride (0.112 g, 0.58 mmol). The reaction was stirred under a nitrogen atmosphere until the reaction was complete (LC/MS) (total of 5 min). The mixture was stirred for an additional 10 min, diluted with dichloromethane (50 mL) and washed with aqueous sodium bicarbonate (5 mL), water (5 ml×2) and brine solution and dried over anhydrous sodium sulfate. The solid was removed by filtration and the solvent removed under vacuum to provide (R)-benzyl 3-(3-chloro-N-(1-(7-chloro-4-oxo-3-(phenylamino)-3,4-dihydroquinazolin-2-yl)but-3-ynyl)-2-fluorobenzamido)propyl-carbamate as an orange solid (0.31 g, 0.45 mmol, 84%). mp 103-105° C. 1H-NMR (DMSO-d6): δ 9.41-8.94 (m, 1H), 8.21-5.62 (m, 16H), 5.35-4.80 (m, 2H), 3.46-1.15 (m, 11H). LC/MS: 686 [M+H].

Aufarbeitung

  1. custom(LC/MS) (total of 5 min)
  2. stirringThe mixture was stirred for an additional 10 min
  3. washwashed with aqueous sodium bicarbonate (5 mL), water (5 ml×2) and brine solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solid was removed by filtration
  6. customthe solvent removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-461b0a56eef04dd1818c3652019073de
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232285B2

Notizen zur Reaktion

Wird geladen…