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Triethylamine → tert-butyl (1-(4-(9H-benzo[f]pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepin-3-yl)benzoyl)piperidin-4-yl)carbamate

HRID 44225
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 44225
[N:1]1[N:2]=[C:3]([C:19]2[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=2)[N:4]2[C:10]=1[C:9]1[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=1[NH:7][C:6]1[N:15]=[CH:16][CH:17]=[CH:18][C:5]2=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[NH:59]1[CH2:64][CH2:63][CH:62]([NH:65][C:66](=[O:72])[O:67][C:68]([CH3:71])([CH3:70])[CH3:69])[CH2:61][CH2:60]1>CN(C=O)C.C(OCC)(=O)C>[N:1]1[N:2]=[C:3]([C:19]2[CH:27]=[CH:26][C:22]([C:23]([N:59]3[CH2:60][CH2:61][CH:62]([NH:65][C:66](=[O:72])[O:67][C:68]([CH3:69])([CH3:71])[CH3:70])[CH2:63][CH2:64]3)=[O:24])=[CH:21][CH:20]=2)[N:4]2[C:10]=1[C:9]1[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=1[NH:7][C:6]1[N:15]=[CH:16][CH:17]=[CH:18][C:5]2=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 7238334-(N-Boc-amino)piperidineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 1361637624-(9H-benzo[f]pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepin-3-yl)benzoic acid

Produkt 1

HCID 136163790
tert-butyl (1-(4-(9H-benzo[f]pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepin-3-yl)benzoyl)piperidin-4-yl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of the 4-(9H-benzo[f]pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepin-3-yl)benzoic acid (0.5 g, 1.4 mmol) in DMF (5 mL) was added HBTU (0.56 g, 1.4 mmol) follwed by triethylamine (0.392 mL, 2.8 mmol). The reaction mixture was stirred at room temperature for 15 minutes then tert-butyl piperidin-4-ylcarbamate (0.31 g, 1.5 mmol) was added and the mixture stirred at room temperature for an additional 3 hours. The mixture was diluted with ethyl acetate (50 mL) and washed with saturated aqueous sodium bicarbonate solution (50 mL) and brine (50 mL). The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography (SiO2, gradient: 50% ethyl acetate in hexanes to 100% ethyl acetate). The tert-butyl (1-(4-(9H-benzo[f]pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepin-3-yl)benzoyl)piperidin-4-yl)carbamate was obtained as a white solid (0.478 g, 63%). M.p.=196-202° C.; 400 MHz 1H NMR (DMSO-d6) δ: 8.81 (br.s, 1H), 8.22 (dd, J=4.4, 1.6 Hz, 1H), 7.97 (dd, J=7.6, 1.6 Hz, 1H), 7.52-7.4 (m, 5H), 7.35 (d, J=8.0 Hz, 1H), 7.19 (dd, J=8.0, 1.2 Hz, 1H), 7.14 (dd, J=7.6, 1.2 Hz, 1H), 6.93 (dd, J=8.0, 1.6 Hz, 1H), 6.89 (br.s, 1H), 4.35-4.25 (m, 1H), 3.6-3.45 (m, 2H), 3.2-3.05 (m, 1H), 3.02-2.9 (m, 1H), 1.9-1.65 (m, 2H), 1.38 (s, 9H), 1.35-1.15 (m, 2H); LCMS [M+H]: 538.

Aufarbeitung

  1. stirringthe mixture stirred at room temperature for an additional 3 hours
  2. washwashed with saturated aqueous sodium bicarbonate solution (50 mL) and brine (50 mL)
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography (SiO2, gradient: 50% ethyl acetate in hexanes to 100% ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-6e2029ba04564da5a8f309af0ef185a6
Quelldatensatz
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08541407B2

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