Pyrazole → HCID 16005346, compound

HRID 2101322Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]2[C:30](=[O:31])[N:12]3[CH:13]=[CH:14][C:15]([C:23]4[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=4)=[C:16]([C:17]4[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=4)[C:11]3=[N:10]2)=[N:6][CH:7]=1.[NH:32]1[CH:36]=[CH:35][CH:34]=[N:33]1.C(=O)([O-])[O-].[K+].[K+].CN(C)CCN>C1(C)C=CC=CC=1.CCOC(C)=O.[Cu]I>[N:32]1([C:2]2[CH:3]=[CH:4][C:5]([CH2:8][N:9]3[C:30](=[O:31])[N:12]4[CH:13]=[CH:14][C:15]([C:23]5[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=5)=[C:16]([C:17]5[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=5)[C:11]4=[N:10]3)=[N:6][CH:7]=2)[CH:36]=[CH:35][CH:34]=[N:33]1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 2-((5-bromopyridin-2-yl)methyl)-7-(4-chlorophenyl)-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (29.6 mg, 0.06 mmol), pyrazole (22.5 mg, 0.33 mmol), copper (I) iodide (8 mg, 0.042 mmol), potassium carbonate (25 mg, 0.18 mmol) and N,N-dimethylethylenediamine (5.3 mg, 0.06 mmol) in 1 mL toluene was heated at 110° C. under argon for 20 h. The reaction mixture was diluted with EtOAc, washed with water, brine, dried (Na2SO4) and concentrated. The crude product was purified by preparative reverse phase HPLC (with TFA) to isolate 1.3 mg of the title compound as a yellow solid. HPLC/MS: retention time=2.44 min, [M+H]+=480.

Workup

washwashed with water, brine
dry with materialdried (Na2SO4)
concentrationconcentrated
customThe crude product was purified by preparative reverse phase HPLC (with TFA)

Sources & evidence

ORD record: ord-6d15592e739442eebe875c4a0a07863e
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572808B2

Reaction notes

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