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Trifluoroacetic acid → HCID 59471847, Verbindung

HRID 2204853
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2204853
C(OC([N:8](C(OC(C)(C)C)=O)[C:9]1[N:10]=[CH:11][C:12]([C:26]2[CH:47]=[CH:46][C:29]([C:30]([N:32]3[CH2:38][CH2:37][CH2:36][N:35](C(OC(C)(C)C)=O)[CH2:34][CH2:33]3)=[O:31])=[CH:28][C:27]=2[C:48]#[N:49])=[N:13][C:14]=1[C:15]1[O:16][C:17]([C:20]2[S:21][CH:22]=[CH:23][C:24]=2[CH3:25])=[N:18][N:19]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl.C(#N)C.CO>[NH2:8][C:9]1[N:10]=[CH:11][C:12]([C:26]2[CH:47]=[CH:46][C:29]([C:30]([N:32]3[CH2:38][CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)=[O:31])=[CH:28][C:27]=2[C:48]#[N:49])=[N:13][C:14]=1[C:15]1[O:16][C:17]([C:20]2[S:21][CH:22]=[CH:23][C:24]=2[CH3:25])=[N:18][N:19]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 6422Trifluoroacetic acid2×HCID 59472333HCID 59472333, Verbindung

Produkt 1

HCID 59471847HCID 59471847, VerbindungAusbeute 43,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 6342AcetonitrileLösungsmittel
HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

tert-Butyl 4-[4-[5-[bis(tert-butoxycarbonyl)amino]-6-[5-(3-methyl-2-thienyl)-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-3-cyano-benzoyl]-1,4-diazepane-1-carboxylate (9.9 g, 11.32 mmol) was dissolved in anhydrous CH2Cl2 (100 mL) at room temperature and TFA (10 mL, 129.8 mmol) added. Additional TFA (10 mL, 129.8 mmol) was added and the reaction mixture stirred at room temperature for 3.5 h and then concentrated in vacuo. The material was dissolved in a mixture of acetonitrile and methanol (10; 1 mixture) and PS—HCO3 (5 eq) added. The mixture was stirred for 1 h at room temperature and then the resin removed by filtration and washed with acetonitrile and methanol. The filtrate was concentrated in vacuo and the residue recrystallised from acetonitrile. The isolated solid was washed with ether and dried to give the product as a yellow solid (2.41 g, 35% yield); 1H NMR (400 MHz, DMSO) d 1.76-1.84 (m, 2H), 2.67 (s, 3H), 2.88-2.93 (m, 4H), 3.42-3.44 (m, 2H), 3.67-3.74 (m, 2H), 7.2 (d, 1H), 7.84-7.87 (m, 1H), 7.89-7.99 (m, 1H), 8.04-8.09 (m, 2H) and 8.85 (s, 1H) ppm; MS (ES+) 487.26

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. additionadded
  3. stirringThe mixture was stirred for 1 h at room temperature
  4. customthe resin removed by filtration
  5. washwashed with acetonitrile and methanol
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue recrystallised from acetonitrile
  8. washThe isolated solid was washed with ether
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-60613701dde249c6be1f1ffe43cd767a
Quelldatensatz
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09365557B2

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