Triethylsilane → 2-((4-Oxo-8-(3-(2'-oxospiro[cyclopropane-1,3'-indoline]-1'-yl)propyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoic acid

HRID 2363006Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2363006
[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][N:9]([CH2:12][CH2:13][CH2:14][N:15]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]4([CH2:25][CH2:24]4)[C:16]3=[O:26])[CH2:8][CH2:7]2)[N:5]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:4][N:3]1[CH2:33][C:34]1[CH:46]=[CH:45][CH:44]=[CH:43][C:35]=1[C:36]([O:38]C(C)(C)C)=[O:37].C([SiH](CC)CC)C>C(O)=O>[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][N:9]([CH2:12][CH2:13][CH2:14][N:15]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]4([CH2:25][CH2:24]4)[C:16]3=[O:26])[CH2:8][CH2:7]2)[N:5]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:4][N:3]1[CH2:33][C:34]1[CH:46]=[CH:45][CH:44]=[CH:43][C:35]=1[C:36]([OH:38])=[O:37]

Komponenten

4

Edukt 2

HCID 12052TriethylsilaneHCID 58046740Tert-butyl 2-((4-oxo-8-(3-(2'-oxospiro[cyclopropane-1,3'-indoline]-1'-yl)propyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate

Produkt 1

HCID 547719832-((4-Oxo-8-(3-(2'-oxospiro[cyclopropane-1,3'-indoline]-1'-yl)propyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 284Formic AcidLösungsmittel

Versuchsvorschrift

To tert-butyl 2-((4-oxo-8-(3-(2′-oxospiro[cyclopropane-1,3′-indoline]-1′-yl)propyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (0.18 g, 0.29 mmol) was added concentrated formic acid (3 mL) and triethylsilane (0.05 mL). After stirring at room temperature for 18 hours, the reaction mixture was concentrated, taken in 4M HCl in dioxane and lyophilized to obtain the title compound as a hydrochloride salt (0.165 g, 95%); 1H NMR (DMSO-d6): δ 1.52-1.63 (m, 4H), 1.98 (d, 2H, J=14.8 Hz), 2.08-2.10 (m, 2H), 2.92 (t, 2H, J=7.6 Hz), 3.21 (br, 2H), 3.45-3.71 (m, 4H), 3.84 (t, 2H, J=6.8 Hz), 4.68 (s, 2H), 4.92 (s, 2H), 6.80 (t, 1H, J=7.6 Hz), 6.98-7.05 (m, 4H), 7.20-7.32 (m, 5H), 7.42 (t, 1H, J=7.6 Hz), 7.57 (t, 1H, J=7.6 Hz), 7.92 (dd, 1H, J=8 and 1.6 Hz), 10.32 (br, 1H), 13.19 (s, 1H); MS for C34H36N4O4 m/z 565.14 (M+H)+.

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-4f4e4b917df14f9d8a0d1f3f551b139b
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08691836B2

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