Diisopropylethylamine → N4,1-dimethyl-N4-((6-methylpyridin-3-yl)methyl)-N5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1H-pyrazole-4,5-dicarboxamide

HRID 1802169Notes

Reaction equation

HRID 1802169 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]([OH:27])=O)[CH:4]=[N:3]1.[CH3:28][NH:29][CH2:30][C:31]1[CH:32]=[N:33][C:34]([CH3:37])=[CH:35][CH:36]=1.C(N(C(C)C)CC)(C)C.CCCP(=O)=O>O1CCCC1>[CH3:28][N:29]([CH2:30][C:31]1[CH:32]=[N:33][C:34]([CH3:37])=[CH:35][CH:36]=1)[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:27]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 154773072-Methyl-5-[(methylamino)methyl]pyridineHCID 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 57377524N4,1-dimethyl-N4-((6-methylpyridin-3-yl)methyl)-N5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1H-pyrazole-4,5-dicarboxamideYield 93.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

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), N-methyl-1-(6-methylpyridin-3-yl)methanamine (50 mg, 367 μmol), diisopropylethylamine (145 μl, 828 μmol) and propylphosphonic anhydride (50% in ethyl acetate, 407 μl, 690 μmol) in tetrahydrofurane (7.00 ml) is stirred for 20 hours at 70° C. under nitrogen atmosphere. 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 N4,1-dimethyl-N4-((6-methylpyridin-3-yl)methyl)-N5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1H-pyrazole-4,5-dicarboxamide (124 mg, 93.5%) as a white solid. mp.: 110-150° C. MS: m/z=481.4 (M+H+).

Workup

  1. customThe solvent is evaporated and to the residue
  2. additionis added sat. aqueous sodium hydrogencarbonate solution
  3. stirringThe mixture is stirred for 20 minutes while a white solid
  4. customprecipitates
  5. filtrationThe solid is collected by filtration
  6. washwashed with diethylether
  7. customdried

Sources & evidence

ORD record
ord-9651ca510c8f4c979465664329bb397c
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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