Pyridine → HCID 50923665, compound

HRID 2179807Notes

Reaction equation

HRID 2179807 reaction equation
[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@@H:4]([CH2:5][CH2:6][C@:7]3([CH3:44])[C@@H:16]2[CH2:15][CH2:14][C@H:13]2[C@@:8]3([CH3:43])[CH2:9][CH2:10][C@@:11]3([C:27]([NH:29][C@@H:30]4[CH2:34][CH2:33][C@H:32]([CH2:35][N:36]5[CH2:41][CH2:40][CH2:39][CH:38]([CH3:42])[CH2:37]5)[CH2:31]4)=[O:28])[CH2:23][CH2:22][C@@H:21]([C:24]([CH3:26])=[CH2:25])[C@@H:12]32)[C:3]1([CH3:46])[CH3:45].N1C=CC=CC=1.[CH3:53][C:54]1([CH3:61])[CH2:58][C:57](=[O:59])[O:56][C:55]1=[O:60]>C(OCC)(=O)C>[CH3:53][C:54]([CH3:61])([CH2:58][C:57](=[O:59])[O:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@@H:4]([CH2:5][CH2:6][C@:7]3([CH3:44])[C@@H:16]2[CH2:15][CH2:14][C@H:13]2[C@@:8]3([CH3:43])[CH2:9][CH2:10][C@@:11]3([C:27](=[O:28])[NH:29][C@@H:30]4[CH2:34][CH2:33][C@H:32]([CH2:35][N:36]5[CH2:41][CH2:40][CH2:39][CH:38]([CH3:42])[CH2:37]5)[CH2:31]4)[CH2:23][CH2:22][C@@H:21]([C:24]([CH3:26])=[CH2:25])[C@@H:12]32)[C:3]1([CH3:45])[CH3:46])[C:55]([OH:60])=[O:56]

Participants

5

Reactant 3

HCID 1049PyridineHCID 870672,2-Dimethylsuccinic anhydrideHCID 50923526HCID 50923526, compound

Product 1

HCID 50923665HCID 50923665, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-N-((1R,3S)-3-((3-methylpiperidin-1-yl)methyl)cyclopentyl)-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxamide (Example −50, 0.24 mmol) in pyridine (5 ml) dimethyl amino pyridine (0.32 g, 0.48 mmol) and 3,3-dimethyldihydrofuran-2,5-dione (1.3 ml) were added and the contents were refluxed for about 16 hours and completion of the reaction monitored by TLC. The reaction mixture was diluted with ethyl acetate (30 ml). The organic layer was washed with 5% aqueous HCl, washed with water followed by brine solution, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography using 5% MeOH in DCM as eluent to furnish the title compound (0.1 g) as a white solid. 1H NMR (300 MHz, CDCl3): 0.80-0.95 (m, 16H) 1.23-1.90 (m, 41H); 2.03-3.08 (m, 16H), 4.13-4.18 (m, 1H), 4.46 (s, 1H), 4.58 (s, 1H), 4.72 (s, 1H); 5.61-5.63 (m, 1H); ES Mass: [M+1] 778 (100%); HPLC: 78.4%.

Workup

  1. temperaturethe contents were refluxed for about 16 hours
  2. washThe organic layer was washed with 5% aqueous HCl
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4c7951e7ff214e1d921741560f88a7bb
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

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