Potassium Carbonate → HCID 14307778, compound

HRID 1769529Notes

Reaction equation

HRID 1769529 reaction equation
[OH:1][C@:2]1([C@:23]2([CH3:24])[C@H:9]([C@H:10]3[C:20](=[CH:21][CH2:22]2)[C@:18]2([CH3:19])[C:13](=[CH:14][C:15](=[O:25])[CH2:16][CH2:17]2)[CH2:12][CH2:11]3)[CH2:8][CH2:7]1)[C:3](=[O:6])[CH2:4]I.[N:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[OH:1][C@:2]1([C@:23]2([CH3:24])[C@H:9]([C@H:10]3[C:20](=[CH:21][CH2:22]2)[C@:18]2([CH3:19])[C:13](=[CH:14][C:15](=[O:25])[CH2:16][CH2:17]2)[CH2:12][CH2:11]3)[CH2:8][CH2:7]1)[C:3](=[O:6])[CH2:4][N:35]1[CH2:36][CH2:37][N:32]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][N:26]=2)[CH2:33][CH2:34]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 944591-(2-Pyridyl)piperazineHCID 14307776HCID 14307776, compound

Product 1

HCID 14307778HCID 14307778, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

17α-Hydroxy-21-iodopregna-4,9(11)-diene-3,20-dione (4.53 g) is stirred in acetonitrile (50 ml) with 1-(2-pyridinyl)piperazine (1.63 g) and potassium carbonate (1.34 g) at 60° for 5 hr and at 20°-25° for 17 hr. The reaction is partitioned between ether and aqueous sodium bicarbonate. The organic phase is washed with saline, dried over sodium sulfate and concentrated. The residue is chromatographed on silica gel with methanol/methylene chloride (4/96) to give the title compound.

Workup

  1. customThe reaction is partitioned between ether and aqueous sodium bicarbonate
  2. washThe organic phase is washed with saline
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue is chromatographed on silica gel with methanol/methylene chloride (4/96)

Sources & evidence

ORD record
ord-ed125a8c3a764d4e8389752b95676d45
Source dataset
uspto-grants-1995_01
Patent number
US05380841

Reaction notes

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