Pyridine → HCID 50925292, compound

HRID 2179786Notes

Reaction equation

HRID 2179786 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([CH2:9][C@H:10]2[CH2:14][CH2:13][C@@H:12]([NH:15][C:16]([C@:18]34[CH2:44][CH2:43][C@@H:42]([C:45]([CH3:47])=[CH2:46])[C@@H:19]3[C@@H:20]3[C@@:33]([CH3:36])([CH2:34][CH2:35]4)[C@@:32]4([CH3:37])[C@@H:23]([C@:24]5([CH3:41])[C@@H:29]([CH2:30][CH2:31]4)[C:28]([CH3:39])([CH3:38])[C@@H:27]([OH:40])[CH2:26][CH2:25]5)[CH2:22][CH2:21]3)=[O:17])[CH2:11]2)[CH2:5][CH2:4]1)[CH3:2].N1C=CC=CC=1.[CH3:54][C:55]1([CH3:62])[CH2:59][C:58](=[O:60])[O:57][C:56]1=[O:61]>C(OCC)(=O)C>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([CH2:9][C@H:10]2[CH2:14][CH2:13][C@@H:12]([NH:15][C:16]([C@:18]34[CH2:44][CH2:43][C@@H:42]([C:45]([CH3:47])=[CH2:46])[C@@H:19]3[C@@H:20]3[C@@:33]([CH3:36])([CH2:34][CH2:35]4)[C@@:32]4([CH3:37])[C@@H:23]([C@:24]5([CH3:41])[C@@H:29]([CH2:30][CH2:31]4)[C:28]([CH3:38])([CH3:39])[C@@H:27]([O:40][C:58](=[O:60])[CH2:59][C:55]([CH3:62])([CH3:54])[C:56]([OH:61])=[O:57])[CH2:26][CH2:25]5)[CH2:22][CH2:21]3)=[O:17])[CH2:11]2)[CH2:5][CH2:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 870672,2-Dimethylsuccinic anhydrideHCID 50925291HCID 50925291, compound

Product 1

HCID 50925292HCID 50925292, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-N-((1R,3S)-3-((4-ethylpiperazin-1-yl)methyl)cyclopentyl)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxamide (Example 35, 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 was 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-a4b0a7e8fa4e4cd480afad0555672564
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

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