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Morpholine → 1-Methyl-4-(morpholine-4-carbonyl)-N-(2-morpholino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1H-pyrazole-5-carboxamide

HRID 1802179
Notes
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Reaction equation

HRID 1802179 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]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)[N:17]=[C:11]3[CH:10]=2)=[C:5]([C:25]([OH:27])=O)[CH:4]=[N:3]1.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.CCCP(=O)=O>O1CCCC1>[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]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)[N:17]=[C:11]3[CH:10]=2)=[O:24])=[C:5]([C:25]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[O:27])[CH:4]=[N:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8083MorpholineHCID 16167369Propylphosphoric anhydrideHCID 677757071-methyl-5-(2-morpholino-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid

Product 1

HCID 573776341-Methyl-4-(morpholine-4-carbonyl)-N-(2-morpholino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1H-pyrazole-5-carboxamideYield 79.3%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

A mixture of 1-methyl-5-(2-morpholino-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid (100 mg, 269 μmol), morpholine (141 μl, 1.62 mmol) and propylphosphonic anhydride (50% in ethyl acetate, 397 μl, 673 μmol) in tetrahydrofurane (7 ml) is refluxed for 18 hours. The solvent is evaporated, the residue diluted with ethyl acetate and washed with sat. aqueous sodium hydrogencarbonate solution and with water. The organic layer is dried with magnesium sulfate and the solvent removed in vacuo affording 1-Methyl-4-(morpholine-4-carbonyl)-N-(2-morpholino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1H-pyrazole-5-carboxamide (94 mg, 79.3%) as a light yellow solid. Mp.: 206-8° C. MS: m/z=441.3 (M+H+).

Workup

  1. temperatureis refluxed for 18 hours
  2. customThe solvent is evaporated
  3. additionthe residue diluted with ethyl acetate
  4. washwashed with sat. aqueous sodium hydrogencarbonate solution and with water
  5. dry with materialThe organic layer is dried with magnesium sulfate
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-873dc4739adb4be2b8547ced3cb25d9a
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08349824B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes