Hydrochloric Acid → N2-hydroxy-7,7-dimethyl-N5-[(1S)-1-phenylethyl]-6,7-dihydrothieno[3,2-c]pyridine-2,5(4H)-dicarboxamide

HRID 468678Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 468678
[CH3:1][C:2]1([CH3:21])[CH2:7][NH:6][CH2:5][C:4]2[CH:8]=[C:9]([C:11]([NH:13][O:14]C3CCCCO3)=[O:12])[S:10][C:3]1=2.C(N(CC)CC)C.[C:29]1([C@@H:35]([N:37]=[C:38]=[O:39])[CH3:36])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.Cl.O1CCOCC1>ClCCCl.O1CCCC1>[OH:14][NH:13][C:11]([C:9]1[S:10][C:3]2[C:2]([CH3:1])([CH3:21])[CH2:7][N:6]([C:38]([NH:37][C@H:35]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH3:36])=[O:39])[CH2:5][C:4]=2[CH:8]=1)=[O:12]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 2724173(S)-(-)-1-Phenylethyl isocyanateHCID 581576817,7-dimethyl-N-(tetrahydro-2H-pyran-2-yloxy)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxamide

Produkt 1

HCID 58157558N2-hydroxy-7,7-dimethyl-N5-[(1S)-1-phenylethyl]-6,7-dihydrothieno[3,2-c]pyridine-2,5(4H)-dicarboxamideAusbeute 47,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 7,7-dimethyl-N-(tetrahydro-2H-pyran-2-yloxy)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxamide (31 mg, 0.1 mmol) and triethylamine (41.8 μL, 0.3 mmol) in 1,2-dichloroethane (1 mL) was added (S)-1-phenylethyl isocyanate (22.1 mg, 0.15 mmol). The reaction was stirred at room temperature overnight. The solution was evaporated to dryness and the residue obtained was redissolved in tetrahydrofuran (1 mL). 4.0 M of hydrochloric acid in 1,4-dioxane (1 mL, 4 mmol) was added and the reaction solution was stirred at room temperature for 2 hours. The solution was evaporated to dryness, redissolved in DMSO (1 mL) and purified on an Agilent 1100 LC/MSD instrument to afford the title compound (17.8 mg, 46%). LCMS (FA) ES+ 374; 1H NMR (400 MHz, MeOD) δ 7.35-7.24 (m, 5H), 7.20-7.15 (m, 1H), 5.01-4.91 (m, 1H), 4.50 (d, J=4.0 Hz, 2H), 3.50 (d, J=4.6 Hz, 2H), 1.47 (d, J=7.1 Hz, 3H), 1.30 (s, 6H).

Aufarbeitung

  1. customThe solution was evaporated to dryness
  2. customthe residue obtained
  3. stirringthe reaction solution was stirred at room temperature for 2 hours
  4. customThe solution was evaporated to dryness
  5. dissolutionredissolved in DMSO (1 mL)
  6. custompurified on an Agilent 1100 LC/MSD instrument

Quellen und Nachweise

ORD-Eintrag
ord-eb325b68e0034beb8ab7f8f5312f9a69
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08624040B2

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