Tetrahydrofuran → HCID 57377412, compound

HRID 1802164Notes

Reaction equation

HRID 1802164 reaction equation
[CH3:1][N:2]1[C:6]([C:7](=[O:24])[NH:8][C:9]2[CH:14]=[CH:13][N:12]3[N:15]=[C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[N:17]=[C:11]3[CH:10]=2)=[C:5]([C:25](O)=[O:26])[CH:4]=[N:3]1.C([N:31]([CH:34]([CH3:36])[CH3:35])CC)(C)C.CCCP(=O)=O.[O:43]1CCC[CH2:44]1>>[CH3:1][N:2]1[C:6]([C:7]([NH:8][C:9]2[CH:14]=[CH:13][N:12]3[N:15]=[C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[N:17]=[C:11]3[CH:10]=2)=[O:24])=[C:5]([C:25]([NH:31][C@@H:34]2[CH2:36][CH2:44][O:43][CH2:35]2)=[O:26])[CH:4]=[N:3]1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 16167369Propylphosphoric anhydrideHCID 573789541-methyl-5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid

Product 1

HCID 57377412HCID 57377412, compoundYield 95.7%

Procedure

A mixture of 1-methyl-5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid (100 mg, 276 μmol), (R)-tetrahydrofuran-3-ylamine4-methylbenzenesulfonate (143 mg, 552 μmol), diisopropylethylamine (193 μl, 1.1 mmol) and propylphosphonic anhydride (50% in ethyl acetate, 407 μl, 690 μmol) in tetrahydrofurane (7 ml) is refluxed for 18 hours. The solvent is evaporated and to the residue is added sat. aqueous sodium hydrogencarbonate solution. The mixture is stirred for 20 minutes while a white solid precipitates. The solid is collected by filtration, washed with diethylether and dried affording (R)-1-methyl-N5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N4-(tetrahydrofuran-3-yl)-1H-pyrazole-4,5-dicarboxamide (114 mg, 95.7%) as a white solid. mp.: >250° C. MS: m/z=432.3 (M+H+).

Workup

  1. temperatureis refluxed for 18 hours
  2. customThe solvent is evaporated and to the residue
  3. additionis added sat. aqueous sodium hydrogencarbonate solution
  4. customprecipitates
  5. filtrationThe solid is collected by filtration
  6. washwashed with diethylether
  7. customdried

Sources & evidence

ORD record
ord-76ec7f16d4084c19a6d84878dbcc4603
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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