Diisopropylethylamine → HCID 57377527, compound

HRID 1802173Notes

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.Cl.CN.[CH:31]([N:34](C(C)C)CC)(C)C.CCCP(=O)=O>O1CCCC1>[CH3:31][NH:34][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

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), methanamine hydrochloride (186 mg, 2.76 mmol), diisopropylethylamine (627 μl, 3.59 mmol) and propylphosphonic anhydride (50% in ethyl acetate, 407 μl, 690 μmol) in tetrahydrofurane (7.00 ml) is stirred for 4 hours at 70° C. and then over the weekend at 25° 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-N5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1H-pyrazole-4,5-dicarboxamide (69 mg, 66.6%) as a white solid. mp.: >250° C. MS: m/z=376.2 (M+H+).

Workup

customat 25° C.
customThe solvent is evaporated and to the residue
additionis added sat. aqueous sodium hydrogencarbonate solution
stirringThe mixture is stirred for 20 minutes while a white solid
customprecipitates
filtrationThe solid is collected by filtration
washwashed with diethylether
customdried

Sources & evidence

ORD record: ord-d61f5d0c00df456fa2f2ac196945cd54
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349824B2

Reaction notes

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