Triethylamine → N-(3-ethyl-1-((1-methyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79380Notes

Reaction equation

[N:1]1[CH:2]=[C:3]([C:10]([OH:12])=O)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.ClC1C=C(Cl)C=C(Cl)C=1C(Cl)=O.C(N(CC)CC)C.[CH2:32]([C:34]1[C:42]2[C:41]([NH2:43])=[CH:40][CH:39]=[CH:38][C:37]=2[N:36]([CH2:44][C:45]2[CH:49]=[CH:48][N:47]([CH3:50])[N:46]=2)[N:35]=1)[CH3:33]>CN1C(=O)CCC1.[OH-].[Na+].CCOC(C)=O>[CH2:32]([C:34]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][C:41]=2[NH:43][C:10]([C:3]2[N:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]3=[N:1][CH:2]=2)=[O:12])[N:36]([CH2:44][C:45]2[CH:49]=[CH:48][N:47]([CH3:50])[N:46]=2)[N:35]=1)[CH3:33]

Participants

Conditions

Temperature: 87 °C

Procedure

To a suspension of imidazo[1,2-a]pyridine-3-carboxylic acid (47.6 mg, 0.294 mmol) in NMP (4 mL) was added 2,4,6-trichlorobenzoyl chloride (45.9 μL, 0.294 mmol) and triethylamine (40.9 μL, 0.294 mmol). The reaction mixture was stirred for 30 minutes. 3-Ethyl-1-((1-methyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-amine (50 mg, 0.196 mmol) was added and the mixture was heated at 87° C. for three hours. The mixture was cooled to ambient temperature and diluted with 10% NaOH aqueous solution (5 mL) and EtOAc (20 mL). The organic phase was washed with water and brine and concentrated under reduced pressure. The residue was triturated with Et2O to give the final product (52 mg). MS (ES+APCI) m/z=400 (M+H).

Workup

temperatureThe mixture was cooled to ambient temperature
washThe organic phase was washed with water and brine
concentrationconcentrated under reduced pressure
customThe residue was triturated with Et2O

Sources & evidence

ORD record: ord-0760290c1a674d74bca94200b7cbeb2b
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841455B2

Reaction notes

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