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Trifluoroacetic acid → 2-Amino-1-{3-[2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl]-azetidin-1-yl}-2-methyl-propan-1-one

HRID 1849392
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1849392
C(OC(=O)[NH:7][C:8]([CH3:38])([CH3:37])[C:9]([N:11]1[CH2:14][CH:13]([C:15]2[CH:36]=[CH:35][C:18]3[C:19]4[N:20]=[C:21]([C:27]5[N:28]([CH:32]([CH3:34])[CH3:33])[N:29]=[CH:30][N:31]=5)[S:22][C:23]=4[CH2:24][CH2:25][O:26][C:17]=3[CH:16]=2)[CH2:12]1)=[O:10])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C:8]([CH3:38])([CH3:37])[C:9]([N:11]1[CH2:12][CH:13]([C:15]2[CH:36]=[CH:35][C:18]3[C:19]4[N:20]=[C:21]([C:27]5[N:28]([CH:32]([CH3:34])[CH3:33])[N:29]=[CH:30][N:31]=5)[S:22][C:23]=4[CH2:24][CH2:25][O:26][C:17]=3[CH:16]=2)[CH2:14]1)=[O:10]
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Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 67050555(2-{3-[2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl]-azetidin-1-yl}-1,1-dimethyl-2-oxo-ethyl)-carbamic acid tert-butyl ester

Produkt 1

HCID 582037892-Amino-1-{3-[2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl]-azetidin-1-yl}-2-methyl-propan-1-oneAusbeute 71,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

To a solution of (2-{3-[2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl]-azetidin-1-yl}-1,1-dimethyl-2-oxo-ethyl)-carbamic acid tert-butyl ester (203 mg, 0.36 mmol) in DCM (2 mL) was added TFA (2 mL) and the reaction mixture was stirred for 1 hour then concentrated in vacuo. The residual solid was triturated with ether, filtered off and air-dried before being dissolved in DCM. The organic solution was washed (aqueous saturated sodium bicarbonate solution, followed by water and then brine), dried (MgSO4) and concentrated in vacuo. The residue was freeze-dried from MeOH/H2O to give 469 as a white solid (116 mg, 71%). LCMS: RT=8.13 min, [M+H]+=453. 1H NMR δ (ppm) (DMSO-d6): 8.30 (1 H, d, J=8.19 Hz), 8.06 (1 H, s), 7.18 (1 H, dd, J=8.24, 1.86 Hz), 7.00 (1 H, d, J=1.82 Hz), 5.82-5.74 (1 H, m), 4.79 (1 H, s), 4.42 (1 H, s), 4.33 (2 H, t, J=5.13 Hz), 4.19 (1 H, s), 3.77-3.70 (2 H, m), 3.39 (2 H, t, J=5.02 Hz), 1.74 (2 H, s), 1.50 (6 H, d, J=6.59 Hz), 1.17 (6 H, s)

Aufarbeitung

  1. concentrationthen concentrated in vacuo
  2. customThe residual solid was triturated with ether
  3. filtrationfiltered off
  4. customair-dried
  5. dissolutionbefore being dissolved in DCM
  6. washThe organic solution was washed (aqueous saturated sodium bicarbonate solution
  7. dry with materialbrine), dried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. dry with materialThe residue was freeze-dried from MeOH/H2O

Quellen und Nachweise

ORD-Eintrag
ord-086bdb7b7be64c03835dfb755fbed6b5
Quelldatensatz
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08952043B2

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