Hydrochloric Acid → HCID 22031054, compound

HRID 1792594Notes

Reaction equation

HRID 1792594 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[N:10]2[CH:11]=[C:12]([C:15]3[C:16]([C:39]4[S:43][C:42]([C:44]([O:46]C)=[O:45])=[CH:41][CH:40]=4)=[N:17][N:18]([C:20]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:19]=3)[CH:13]=[CH:14][C:9]2=[N:8][CH:7]=1.[OH-].[Li+].C(O)C.Cl>O>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[N:10]2[CH:11]=[C:12]([C:15]3[C:16]([C:39]4[S:43][C:42]([C:44]([OH:46])=[O:45])=[CH:41][CH:40]=4)=[N:17][N:18]([C:20]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:19]=3)[CH:13]=[CH:14][C:9]2=[N:8][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 3939Lithium HydroxideHCID 22032135HCID 22032135, compound

Product 1

HCID 22031054HCID 22031054, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

1.20 g methyl 5-{4-[3-(1,3-thiazol-2-yl)imidazo-[1,2-a)pyridin-6-yl]-1-trityl-1H-3-pyrazolyl}-2-thiophene carboxylate obtained in Example 442, 0.16 g lithium hydroxide, 30 mL ethanol and 15 mL water were heated at 85° C. for 5 hours. Under ice-cooling, the reaction solution was neutralized by adding water and 1 N aqueous hydrochloric acid and then extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate. The drying agent was removed, and the solvent was concentrated, whereby 1.08 g of the title compound was obtained as a white solid.

Workup

  1. temperatureUnder ice-cooling
  2. extractionextracted with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. customThe drying agent was removed
  5. concentrationthe solvent was concentrated

Sources & evidence

ORD record
ord-0775a214685d4d79b73aba71e9b6fd1b
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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