HCID 68275967, Verbindung → HCID 68357904, Verbindung

HRID 85558

Reaktionsgleichung

[N:1]([C@:4]12[CH2:39][CH2:38][C@@H:37]([C:40]([CH3:42])=[CH2:41])[C@@H:5]1[C@@H:6]1[C@@:19]([CH3:22])([CH2:20][CH2:21]2)[C@@:18]2([CH3:23])[C@@H:9]([C@:10]3([CH3:36])[C@@H:15]([CH2:16][CH2:17]2)[C:14]([CH3:25])([CH3:24])[C:13]([C:26]2[CH:35]=[CH:34][C:29]([C:30]([O:32]C)=[O:31])=[CH:28][CH:27]=2)=[CH:12][CH2:11]3)[CH2:8][CH2:7]1)=[C:2]=[O:3].CN(C)CCNC(=O)N[C@]12CC[C@@H](C(C)=C)[C@@H]1[C@@H]1[C@@](C)(CC2)[C@@]2(C)[C@@H]([C@]3(C)[C@@H](CC2)C(C)(C)C(C2C=CC(C(O)=O)=CC=2)=CC3)CC1.[CH3:90][N:91]([CH3:103])[C@H:92]1[C@H:96]([N:97]2[CH2:102][CH2:101][NH:100][CH2:99][CH2:98]2)[CH2:95][O:94][CH2:93]1>>[CH3:90][N:91]([CH3:103])[C@@H:92]1[CH2:93][O:94][CH2:95][C@H:96]1[N:97]1[CH2:102][CH2:101][N:100]([C:2]([NH:1][C@:4]23[CH2:39][CH2:38][C@@H:37]([C:40]([CH3:42])=[CH2:41])[C@@H:5]2[C@@H:6]2[C@@:19]([CH3:22])([CH2:20][CH2:21]3)[C@@:18]3([CH3:23])[C@@H:9]([C@:10]4([CH3:36])[C@@H:15]([CH2:16][CH2:17]3)[C:14]([CH3:24])([CH3:25])[C:13]([C:26]3[CH:27]=[CH:28][C:29]([C:30]([OH:32])=[O:31])=[CH:34][CH:35]=3)=[CH:12][CH2:11]4)[CH2:8][CH2:7]2)=[O:3])[CH2:99][CH2:98]1

Komponenten

Edukt 3

HCID 68275967HCID 68275967, Verbindung

HCID 683578464-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(3-(2-(dimethylamino)ethyl)ureido)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoic acid

HCID 86676572methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-isocyanato-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate

Produkt 1

HCID 68357904HCID 68357904, VerbindungAusbeute 20 %

Versuchsvorschrift

The title compound was prepared in 20% yield from methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-isocyanato-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate following the same procedure as described for the preparation of 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(3-(2-(dimethylamino)ethyl)ureido)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoic acid, except (3S,4S)—N,N-dimethyl-4-(piperazin-1-yl)tetrahydrofuran-3-amine was used instead of N,N-dimethylethylenediamine in Step 1. LCMS: m/e 755.6 (M+H)+, 1.85 min (method 6). 1H NMR (500 MHz, METHANOL-d4) δ=7.93 (d, J=8.2 Hz, 2H), 7.23 (d, J=8.2 Hz, 2H), 5.31 (d, J=6.1 Hz, 1H), 4.78 (s, 1H), 4.64 (br. s., 1H), 4.09 (d, J=3.4 Hz, 1H), 4.05 (d, J=4.9 Hz, 2H), 4.02 (td, J=3.5, 6.8 Hz, 1H), 3.96 (td, J=5.1, 10.1 Hz, 1H), 3.73 (d, J=5.2 Hz, 1H), 3.56-3.41 (m, 4H), 2.96 (s, 6H), 2.87-2.66 (m, 5H), 2.59 (d, J=13.1 Hz, 1H), 2.45 (dd, J=8.7, 11.7 Hz, 1H), 2.16 (dd, J=6.4, 17.1 Hz, 1H), 1.97-1.90 (m, 1H), 1.90-1.82 (m, 1H), 1.82-1.74 (m, 2H), 1.73 (s, 3H), 1.66-1.54 (m, 3H), 1.51 (d, J=12.5 Hz, 4H), 1.45-1.26 (m, 6H), 1.23-1.15 (m, 2H), 1.13 (s, 3H), 1.10 (d, J=13.4 Hz, 2H), 1.06 (s, 3H), 1.04 (s, 3H), 0.97 (s, 3H), 0.95 (s, 3H).

Aufarbeitung

customm/e 755.6 (M+H)+, 1.85 min (method 6)

Quellen und Nachweise

ORD-Eintrag: ord-e1379fa79a9b4bae902a3ed385e9c711
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08846647B2

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