3-Methoxypropylamine → HCID 57377413, compound

HRID 1802165Notes

Reaction equation

HRID 1802165 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.[CH3:28][O:29][CH2:30][CH2:31][CH2:32][NH2:33].CCCP(=O)=O>O1CCCC1>[CH3:28][O:29][CH2:30][CH2:31][CH2:32][NH:33][C:25]([C:5]1[CH:4]=[N:3][N:2]([CH3:1])[C:6]=1[C:7]([NH:8][C:9]1[CH:14]=[CH:13][N:12]2[N:15]=[C:16]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:17]=[C:11]2[CH:10]=1)=[O:24])=[O:26]

Participants

5

Reactant 3

HCID 16723-MethoxypropylamineHCID 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 57377413HCID 57377413, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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), 3-methoxypropan-1-amine (169 μl, 1.66 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 N4-(3-Methoxypropyl)-1-methyl-N5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1H-pyrazole-4,5-dicarboxamide (113 mg, 94.3%) as a white solid. mp.: 191-3° C. MS: m/z=434.4 (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-fef12037cf2e4b568640cd5d8e0a7149
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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