Potassium Hydroxide → HCID 112500221, compound

HRID 515925Notes

Reaction equation

HRID 515925 reaction equation
[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]([C:45]2[CH:46]=[N:47][N:48]([CH3:50])[CH:49]=2)[C:16]([C:18]2[CH:22]=[C:21]([C:23]3[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:24]=3[C:30]([N:32]3[C@H:41]([CH3:42])[CH2:40][C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[CH2:33]3)=[O:31])[N:20]([CH3:43])[C:19]=2[CH3:44])=[O:17])=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.[OH-].[K+]>CO.ClCCl>[Cl:29][C:27]1[CH:26]=[CH:25][C:24]([C:30]([N:32]2[C@H:41]([CH3:42])[CH2:40][C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH2:33]2)=[O:31])=[C:23]([C:21]2[N:20]([CH3:43])[C:19]([CH3:44])=[C:18]([C:16]([N:15]([C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=3)[C:45]3[CH:46]=[N:47][N:48]([CH3:50])[CH:49]=3)=[O:17])[CH:22]=2)[CH:28]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 131733322HCID 131733322, compound

Product 1

HCID 112500221HCID 112500221, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.8 g of the compound obtained in Step C (1.03 mmol) in 2 mL of methanol, there are added 1.55 mL of a 1M solution of potassium hydroxide in methanol (1.55 mmol). The batch is stirred at ambient temperature for 30 minutes. The reaction mixture is then diluted with dichloromethane and successively washed with 1M aqueous HCl solution, saturated aqueous NaHCO3 solution and then brine until neutral. The organic phase is then dried over MgSO4, filtered and evaporated. The crude product thereby obtained is purified by chromatography over silica gel using dichloromethane and methanol as eluants. The solid thereby obtained is dissolved in a mixture of water/acetonitrile until dissolution is complete, filtered and then lyophilised.

Workup

  1. washsuccessively washed with 1M aqueous HCl solution, saturated aqueous NaHCO3 solution
  2. dry with materialThe organic phase is then dried over MgSO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-c2bde1c59f04497a9bfc12a4a41b4775
Source dataset
uspto-grants-2015_08
Patent number
US09108983B2

Reaction notes

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