Sodium hydride → HCID 23660305, Verbindung

HRID 1435447Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1435447
[CH:1]1([NH:4][C:5]([C:7]2[CH:11]=[CH:10][NH:9][CH:8]=2)=[O:6])[CH2:3][CH2:2]1.[H-].[Na+].[C:14]([C:18]1[N:22]([CH2:23][CH:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[C:21]2[CH:30]=[CH:31][C:32]([S:34](Cl)(=[O:36])=[O:35])=[CH:33][C:20]=2[N:19]=1)([CH3:17])([CH3:16])[CH3:15]>C1COCC1.CN(C=O)C>[C:14]([C:18]1[N:22]([CH2:23][CH:24]2[CH2:25][CH2:26][O:27][CH2:28][CH2:29]2)[C:21]2[CH:30]=[CH:31][C:32]([S:34]([N:9]3[CH:10]=[CH:11][C:7]([C:5]([NH:4][CH:1]4[CH2:3][CH2:2]4)=[O:6])=[CH:8]3)(=[O:35])=[O:36])=[CH:33][C:20]=2[N:19]=1)([CH3:17])([CH3:15])[CH3:16]

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 579372982-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chlorideHCID 57937310N-cyclopropyl-1H-pyrrole-3-carboxamide

Produkt 1

HCID 23660305HCID 23660305, VerbindungAusbeute 51,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Following the same procedure in Example 29, using N-cyclopropyl-1H-pyrrole-3-carboxamide (49 mg, 0.33 mmol) (see following step B for preparation), sodium hydride (100 mg, 60%, 2.5 mmol) and 2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride (122 mg, 0.33 mmol) in THF (6 mL) and DMF (0.5 mL). The crude product was purified by MPLC using Hex/EtOAc (1:4) on silica gel to give 82 mg (51%) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 0.50-0.56 (m, 2 H), 0.69-0.76 (m, 2 H), 1.40-1.57 (m, 4 H), 1.59 (s, 9 H), 2.29 (m, 1 H), 2.67-2.76 (m, 1 H), 3.24-3.34 (m, 2 H), 3.84-3.93 (m, 2 H), 4.41 (d, J=7.42 Hz, 2 H), 6.64 (dd, J=3.32, 1.56 Hz, 1 H), 7.27 (dd, J=3.32, 2.34 Hz, 1 H), 7.78-7.82 (m, 1 H), 7.90 (d, J=9.0 Hz, 1 H), 7.94 (dd, J=8.6, 1.5 Hz, 1H), 8.25 (d, J=1.56 Hz, 1 H); MS (ESI) (M+H)+=484.7; Anal. Calcd for C25H32N4O4S+1.10 TFA+0.10H2O (611.88): C, 53.40; H, 5.49; N, 9.16. Found: C, 53.44; H, 5.53; N, 9.18.

Aufarbeitung

  1. customThe crude product was purified by MPLC

Quellen und Nachweise

ORD-Eintrag
ord-1d4673a114a64365aeb73c393e7874f9
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07615642B2

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