2-Chloro-N,N-dimethylethylamine → 4-((1S,3aS,5aR,5bR,7aS,9S,11aS,11bR,13aR,13bR)-3a-((2-(dimethylamino)ethyl)amino)-1-isopropyl-5a,5b,8,8,11a-pentamethylicosahydro-1H-cyclopenta[a]chrysen-9-yl)benzoic acid

HRID 85708Notes

Reaction equation

HRID 85708 reaction equation
O=S1(=O)C[CH2:6][N:5]([CH2:8][CH2:9][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)[CH2:4]C1.ClCCN(C)C>>[CH3:6][N:5]([CH3:4])[CH2:8][CH2:9][NH:10][C@:11]12[CH2:45][CH2:44][C@@H:43]([CH:46]([CH3:47])[CH3:48])[C@@H:12]1[C@@H:13]1[C@@:26]([CH3:29])([CH2:27][CH2:28]2)[C@@:25]2([CH3:30])[C@@H:16]([C@:17]3([CH3:42])[C@@H:22]([CH2:23][CH2:24]2)[C:21]([CH3:32])([CH3:31])[C@@H:20]([C:33]2[CH:41]=[CH:40][C:36]([C:37]([OH:39])=[O:38])=[CH:35][CH:34]=2)[CH2:19][CH2:18]3)[CH2:15][CH2:14]1

Participants

3

Reactant 2

HCID 79012-Chloro-N,N-dimethylethylamineHCID 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

Product 1

HCID 683578834-((1S,3aS,5aR,5bR,7aS,9S,11aS,11bR,13aR,13bR)-3a-((2-(dimethylamino)ethyl)amino)-1-isopropyl-5a,5b,8,8,11a-pentamethylicosahydro-1H-cyclopenta[a]chrysen-9-yl)benzoic acid

Procedure

The title compound was prepared following the method described 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 2-chloro-N,N-dimethylethanamine as the alkylating reagent in Step 3. The product was isolated as a colorless oil (0.9 mg, 37%). LCMS: m/e 605.56 (M+H)+, 2.35 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), 3.89-3.72 (m, 2H), 3.70-3.55 (m, 1H), 3.07-2.91 (m, 1H), 3.00 (s, 6H), 2.60-2.40 (m, 1H), 2.34-1.04 (m, 26H), 1.18 (s, 3H), 1.12 (s, 3H), 1.07 (s, 3H), 0.93 (d, J=6.7 Hz, 3H), 0.86 (d, J=6.7 Hz, 3H), 0.83 (s, 3H), 0.79 (s, 3H).

Sources & evidence

ORD record
ord-fbf1fc223107402e9da8b902c239fa18
Source dataset
uspto-grants-2014_09
Patent number
US08846647B2

Reaction notes

Loading…