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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57991863, Verbindung

HRID 2075362
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2075362
C(OC([C@@H:8]([C@@H:12]([C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=1)[CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[C:9]([OH:11])=O)=O)(C)(C)C.CC[N:34]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH:53]1[C:62]2[C:57](=[CH:58][C:59]([C:63]3[S:67][C:66]([NH2:68])=[N:65][N:64]=3)=[CH:60][CH:61]=2)[CH:56]=[CH:55][N:54]=1.[CH:69]1[C:78]2[C:73](=CC(C(O)=O)=C[CH:77]=2)C=CN=1.ClC1C=NC=C2SC([C:92]([OH:94])=[O:93])=CC=12>CN(C=O)C>[CH:53]1[C:62]2[C:57](=[CH:58][C:59]([C:63]3[S:67][C:66]([NH2:68])=[N:65][N:64]=3)=[CH:60][CH:61]=2)[CH:56]=[CH:55][N:54]=1.[Si:15]([O:14][CH2:13][C@@H:12]([C:22]1[CH:23]=[CH:24][C:25]([C:28]([F:30])([F:31])[F:29])=[CH:26][CH:27]=1)[C@H:8]([NH:34][C:92](=[O:93])[O:94][C:78]([CH3:77])([CH3:69])[CH3:73])[C:9]([NH:68][C:66]1[S:67][C:63]([C:59]2[CH:58]=[C:57]3[C:62](=[CH:61][CH:60]=2)[CH:53]=[N:54][CH:55]=[CH:56]3)=[N:64][N:65]=1)=[O:11])([C:18]([CH3:21])([CH3:19])[CH3:20])([CH3:16])[CH3:17]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 6

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 185161084-Chlorothieno[2,3-c]pyridine-2-carboxylic acidHCID 22128831Isoquinoline-6-carboxylic acidHCID 596944465-(Isoquinolin-6-yl)-1,3,4-thiadiazol-2-amineHCID 67089215HCID 67089215, Verbindung

Produkt 2

HCID 57991863HCID 57991863, VerbindungAusbeute 54 %HCID 596944465-(Isoquinolin-6-yl)-1,3,4-thiadiazol-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To (2S,3S)-2-(tert-butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)-3-(4-(trifluoromethyl)phenyl)butanoic acid (0.11 g, 0.23 mmol) in 3 mL of DMF was added EDCI (0.065 g, 0.34 mmol) and HOBt (0.062 g, 0.46 mmol). After 10 minutes, 5-(isoquinolin-6-yl)-1,3,4-thiadiazol-2-amine (0.057 g, 0.25 mmol) was added. 5-(isoquinolin-6-yl)-1,3,4-thiadiazol-2-amine was prepared as shown in Scheme 5 using isoquinoline-6-carboxylic acid, commercially available from AstaTech Product List (Order Number 62874), instead of 4-chlorothieno[2,3-c]pyridine-2-carboxylic acid. The mixture was stirred for 12 hours. The solvent was removed under reduced pressure and the residue was taken up in 20 mL of EtOAc. The mixture was washed with aq NH4Cl (5 mL), water (5×5 mL), and brine (5 mL), then dried over MgSO4. The mixture was filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (eluting with a gradient from 0 to 2.5% MeOH in DCM) to provide tert-butyl (2S,3S)-4-(tert-butyldimethylsilyloxy)-1-(5-(isoquinolin-6-yl)-1,3,4-thiadiazol-2-ylamino)-1-oxo-3-(4-trifluoromethylphenyl)butan-2-ylcarbamate (0.086 g, 54%) as a yellow solid. 1H NMR (400 MHz, CD3OD): δ ppm 9.38 (s, 1H), 8.61-8.58 (m, 2H), 8.40 (d, J=8.9, 1H), 8.32 (d, 8.6 Hz, 1H), 8.06 (s, 1H), 8.04 (d, J=5.8 Hz, 1H), 7.70 (d, J=7.9 Hz, 2H), 7.61 (d, J=8.1 Hz, 2H), 5.01-4.95 (m, 1H), 4.11-3.96 (m, 2H), 3.62-3.55 (m, 1H), 1.38 (s, 9H), 0.87 (s, 9H), 0.02 (s, 3H), 0.00 (s, 3H). 1H not detected.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. washThe mixture was washed with aq NH4Cl (5 mL), water (5×5 mL), and brine (5 mL)
  3. dry with materialdried over MgSO4
  4. filtrationThe mixture was filtered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (
  7. washeluting with a gradient from 0 to 2.5% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-28a234ec55764686a4f89044d123c294
Quelldatensatz
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07919504B2

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