Methanol → HCID 22031644, compound

HRID 1792585Notes

Reaction equation

HRID 1792585 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]2[CH:12]=[C:13]([C:16]3[C:17]([C:40]([O:42]C)=[O:41])=[N:18][N:19]([C:21]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:20]=3)[CH:14]=[CH:15][C:10]2=[N:9][CH:8]=1.[OH-].[Na+].CO.[Cl-].[NH4+]>O.C(OCC)(=O)C.O1CCCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]2[CH:12]=[C:13]([C:16]3[C:17]([C:40]([OH:42])=[O:41])=[N:18][N:19]([C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)([C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)[C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH:20]=3)[CH:14]=[CH:15][C:10]2=[N:9][CH:8]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 22031150HCID 22031150, compound

Product 1

HCID 22031644HCID 22031644, compoundYield 77.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 228 mg methyl 4-[3-(pyridin-2-yl)imidazo-[1,2-a]pyridin-6-yl]-1-trityl-1H-pyrazole-3-carboxylate (compound in Example 366), 0.8 mL of 1 N aqueous sodium hydroxide, 5 mL methanol and 3 mL tetrahydrofuran was stirred at 50° C. for 4 hours. Saturated ammonium chloride, ethyl acetate and water were added to the reaction solution, and then the organic layer was separated, washed with brine and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was evaporated. The resulting residue was crystallized from diisopropyl ether, triturated and dried under reduced pressure with a vacuum pump, to give 172 mg 4-[3-(pyridin-2-yl)imidazo-[1,2-a]pyridin-6-yl]-1-trityl-1H-pyrazole-3-carboxylic acid as pale brown crystals. From this carboxylic acid derivative, 78 mg of the title compound was obtained as a pale yellow amorphous under the same conditions as in Example 361.

Workup

  1. customthe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe drying agent was filtered off
  5. customthe filtrate was evaporated
  6. customThe resulting residue was crystallized from diisopropyl ether
  7. customtriturated
  8. customdried under reduced pressure with a vacuum pump

Sources & evidence

ORD record
ord-4cb83f7b081542a18c833fe5a28d29f9
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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