4-((1S,3aS,5aR,5bR,7aS,9S,11aS,11bR,13aR,13bR)-3a-((2-(1,1-dioxidothiomorpholino)ethyl)amino)-1-isopropyl-5a,5b,8,8,11a-pentamethylicosahydro-1H-cyclopenta[a]chrysen-9-yl)benzoic acid → 4-((1S,3aS,5aR,5bR,7aS,9S,11aS,11bR,13aR,13bR)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-3a-((2-(4-(methylsulfonyl)piperidin-1-yl)ethyl)amino)icosahydro-1H-cyclopenta[a]chrysen-9-yl)benzoic acid

HRID 85730Notes

Reaction equation

O=S1(=O)CCN(CC[NH:10][C@:11]23[CH2:45][CH2:44][C@@H:43]([CH:46]([CH3:48])[CH3:47])[C@@H:12]2[C@@H:13]2[C@@:26]([CH3:29])([CH2:27][CH2:28]3)[C@@:25]3([CH3:30])[C@@H:16]([C@:17]4([CH3:42])[C@@H:22]([CH2:23][CH2:24]3)[C:21]([CH3:32])([CH3:31])[C@@H:20]([C:33]3[CH:41]=[CH:40][C:36]([C:37]([OH:39])=[O:38])=[CH:35][CH:34]=3)[CH2:19][CH2:18]4)[CH2:15][CH2:14]2)CC1.Cl[CH2:51][CH2:52][N:53]1[CH2:58][CH2:57][CH:56]([S:59]([CH3:62])(=[O:61])=[O:60])[CH2:55][CH2:54]1>>[CH:46]([C@H:43]1[C@@H:12]2[C@@H:13]3[C@@:26]([CH3:29])([CH2:27][CH2:28][C@@:11]2([NH:10][CH2:51][CH2:52][N:53]2[CH2:58][CH2:57][CH:56]([S:59]([CH3:62])(=[O:61])=[O:60])[CH2:55][CH2:54]2)[CH2:45][CH2:44]1)[C@@:25]1([CH3:30])[C@@H:16]([C@:17]2([CH3:42])[C@@H:22]([CH2:23][CH2:24]1)[C:21]([CH3:32])([CH3:31])[C@@H:20]([C:33]1[CH:41]=[CH:40][C:36]([C:37]([OH:39])=[O:38])=[CH:35][CH:34]=1)[CH2:19][CH2:18]2)[CH2:15][CH2:14]3)([CH3:48])[CH3:47]

Participants

Reactant 2

HCID 601523744-((1S,3aS,5aR,5bR,7aS,9S,11aS,11bR,13aR,13bR)-3a-((2-(1,1-dioxidothiomorpholino)ethyl)amino)-1-isopropyl-5a,5b,8,8,11a-pentamethylicosahydro-1H-cyclopenta[a]chrysen-9-yl)benzoic acid

HCID 682759471-(2-Chloroethyl)-4-(methylsulfonyl)piperidine

Product 1

HCID 712453324-((1S,3aS,5aR,5bR,7aS,9S,11aS,11bR,13aR,13bR)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-3a-((2-(4-(methylsulfonyl)piperidin-1-yl)ethyl)amino)icosahydro-1H-cyclopenta[a]chrysen-9-yl)benzoic acid

Procedure

The title compound was prepared following the method described in above for the synthesis of 4-((1S,3aS,5aR,5bR,7aS,9S,11aS,11bR,13aR,13bR)-3a-((2-(1,1-dioxidothiomorpholino)ethyl)amino)-1-isopropyl-5a,5b,8,8,11a-pentamethylicosahydro-1H-cyclopenta[a]chrysen-9-yl)benzoic acid using 1-(2-chloroethyl)-4-(methylsulfonyl)piperidine (prepared as described below) as the alkylating reagent in Step 3. The product was isolated as a white solid (24 mg, 36%). LCMS: m/e 723.56 (M+H)+, 2.28 min (method 11). 1H NMR (500 MHz, Acetic) δ 8.02 (d, J=8.2 Hz, 2H), 7.36 (d, J=8.2 Hz, 2H), 3.77-3.63 (m, 2H), 3.62-3.54 (m, 3H), 3.50 (d, J=5.5 Hz, 1H), 3.35 (td, J=11.4, 3.7 Hz, 1H), 3.08-2.89 (m, 2H), 3.02 (s, 3H), 2.50 (d, J=13.1 Hz, 1H), 2.42-2.29 (m, 2H), 2.28-1.03 (m, 28H), 1.21 (s, 3H), 1.12 (s, 3H), 1.08 (s, 3H), 1.01 (d, J=11.3 Hz, 1H), 0.93 (d, J=6.7 Hz, 4H), 0.86 (d, J=6.7 Hz, 4H), 0.83 (s, 3H), 0.79 (s, 3H).

Sources & evidence

ORD record: ord-4125a6643c8d4c218acd18334dce6cfb
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846647B2

Reaction notes

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