N,N-Dimethylethylenediamine → HCID 67776251, compound

HRID 2405482Notes

Reaction equation

HRID 2405482 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].[CH3:7][C@:8]12[C@@:25]3([CH3:26])[C@@H:16]([C@:17]4([CH3:30])[C@@H:22]([CH2:23][CH2:24]3)[C:21]([CH3:28])([CH3:27])[C:20](=[O:29])[CH2:19][CH2:18]4)[CH2:15][CH2:14][C@@H:13]1[C@H:12]1[C@H:31]([C:34]([CH3:36])=[CH2:35])[CH2:32][CH2:33][C@:11]1([C:37](Cl)=[O:38])[CH2:10][CH2:9]2>CN(C1C=CN=CC=1)C.ClCCl>[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH:5][C:37]([C@:11]12[CH2:33][CH2:32][C@@H:31]([C:34]([CH3:36])=[CH2:35])[C@@H:12]1[C@@H:13]1[C@@:8]([CH3:7])([CH2:9][CH2:10]2)[C@@:25]2([CH3:26])[C@@H:16]([C@:17]3([CH3:30])[C@@H:22]([CH2:23][CH2:24]2)[C:21]([CH3:28])([CH3:27])[C:20](=[O:29])[CH2:19][CH2:18]3)[CH2:15][CH2:14]1)=[O:38]

Participants

5

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 86666174HCID 86666174, compound

Product 1

HCID 67776251HCID 67776251, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of N1,N1-dimethylethane-1,2-diamine (74.5 mg, 0.845 mmol), Hunig'sBase (0.369 mL, 2.114 mmol) and DMAP (5.16 mg, 0.042 mmol) in dichloromethane (2 mL) was added (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-9-oxo-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carbonyl chloride (200 mg, 0.423 mmol). The reaction mixture was stirred for 16 h. LCMS indicated the formation of desired product. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in methanol and the clear solution was purified by prep HPLC to provide the title compound as a colorless oil (150 mg, 68%). LCMS: m/e 525.56 (M+H)+, 2.27 min (method 1). 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 6.89 (t, J=5.04 Hz, 1H), 4.72 (d, J=2.14 Hz, 1H), 4.58 (s, 1H), 3.59-3.34 (m, 2H), 3.12 (td, J=11.06, 4.12 Hz, 1H), 2.67 (t, J=5.80 Hz, 2H), 2.53-2.43 (m, 2H), 2.41 (s, 6H), 2.40-2.32 (m, 1H), 2.07-2.03 (m, 1H), 1.97-1.84 (m, 2H), 1.78 (dd, J=11.60, 7.93 Hz, 1H), 1.71 (dd, J=13.12, 2.44 Hz, 1H), 1.67 (s, 3H), 1.62-1.22 (m, 14H), 1.21-1.11 (m, 1H), 1.06 (s, 3H), 1.01 (s, 3H), 1.04-0.97 (m, 1H), 0.97 (s, 6H), 0.91 (s, 3H).

Sources & evidence

ORD record
ord-400c16abec674267b71ca9c99d28758f
Source dataset
uspto-grants-2014_08
Patent number
US08802661B2

Reaction notes

Loading…