Azetidine → 4-(azetidine-1-carbonyl)-N-(2-bromo-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1-methyl-1H-pyrazole-5-carboxamide

HRID 1802251Notes

Reaction equation

[Br:1][C:2]1[N:22]=[C:5]2[CH:6]=[C:7]([NH:10][C:11]([C:13]3[N:17]([CH3:18])[N:16]=[CH:15][C:14]=3[C:19]([OH:21])=O)=[O:12])[CH:8]=[CH:9][N:4]2[N:3]=1.[NH:23]1[CH2:26][CH2:25][CH2:24]1.CCCP(=O)=O.C(N(CC)C(C)C)(C)C>O1CCCC1>[Br:1][C:2]1[N:22]=[C:5]2[CH:6]=[C:7]([NH:10][C:11]([C:13]3[N:17]([CH3:18])[N:16]=[CH:15][C:14]=3[C:19]([N:23]3[CH2:26][CH2:25][CH2:24]3)=[O:21])=[O:12])[CH:8]=[CH:9][N:4]2[N:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 5-(2-bromo-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylic acid (929 mg, 2.54 mmol), azetidine (206 μl, 3.05 mmol), propylphosphonic anhydride (50% in ethyl acetate, 3.75 ml, 6.36 mmol) and N,N-diisopropylethylamine (1.3 ml, 7.63 mmol) in tetrahydrofuran (20 ml) was stirred for 18 hours at 25° C. The solvent was evaporated, the residue was triturated with sat. sodium hydrogencarbonate solution. The solid was filtered off, washed with water and dried in vacuo affording 4-(azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carboxylic acid (2-bromo-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-amide (910 mg, 88.5%) as a light yellow solid. mp: >250° C., MS: m/z=402.2/404.0 (M−H+)

Workup

customThe solvent was evaporated
customthe residue was triturated with sat. sodium hydrogencarbonate solution
filtrationThe solid was filtered off
washwashed with water
customdried in vacuo

Sources & evidence

ORD record: ord-301c1e42282849308140301a357c9812
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349824B2

Reaction notes

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