Diisopropylethylamine → HCID 67779881, compound

HRID 1802219Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:16]=[C:10]3[CH:11]=[C:12]([NH2:15])[CH:13]=[CH:14][N:9]3[N:8]=2)[CH:2]=1.[CH3:17][O:18][C:19]([C:21]1[CH:22]=[N:23][N:24]([CH3:29])[C:25]=1[C:26](O)=[O:27])=[O:20].CCCP(=O)=O.C(N(CC)C(C)C)(C)C>O1CCCC1>[CH3:29][N:24]1[C:25]([C:26](=[O:27])[NH:15][C:12]2[CH:13]=[CH:14][N:9]3[N:8]=[C:7]([C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)[N:16]=[C:10]3[CH:11]=2)=[C:21]([C:19]([O:18][CH3:17])=[O:20])[CH:22]=[N:23]1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 2-(pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-amine (468 mg, 2.22 mmol), 4-(methoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acid (490 mg, 2.66 mmol), propylphosphonic anhydride (50% in ethyl acetate, 3.26 ml, 5.54 mmol) and N,N-diisopropylethylamine (1.51 ml, 8.86 mmol) in tetrahydrofurane (15 ml) is stirred for 18 hours at 70° C. under nitrogen atmosphere. The solvent is evaporated and the residue triturated with sat. aqueous sodium bicarbonate solution. The solid is collected by filtration, washed with water and dried affording methyl 1-methyl-5-(2-(pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylate (564 mg, 67.5%) as a light brown solid. mp.: 228-231° C. MS: m/z=378.5 (M+H+).

Workup

customThe solvent is evaporated
customthe residue triturated with sat. aqueous sodium bicarbonate solution
filtrationThe solid is collected by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-3aa353ae5b2d407083d42b0cc2f55b7e
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349824B2

Reaction notes

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