Triethylamine → N-(1-((1,5-dimethyl-1H-pyrazol-3-yl)methyl)-3-ethyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79374

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.[CH3:32][N:33]1[C:37]([CH3:38])=[CH:36][C:35]([CH2:39][N:40]2[C:48]3[CH:47]=[CH:46][CH:45]=[C:44]([NH2:49])[C:43]=3[C:42]([CH2:50][CH3:51])=[N:41]2)=[N:34]1>CN1C(=O)CCC1.[OH-].[Na+].CCOC(C)=O>[CH3:32][N:33]1[C:37]([CH3:38])=[CH:36][C:35]([CH2:39][N:40]2[C:48]3[C:43](=[C:44]([NH:49][C:10]([C:3]4[N:4]5[CH:9]=[CH:8][CH:7]=[CH:6][C:5]5=[N:1][CH:2]=4)=[O:12])[CH:45]=[CH:46][CH:47]=3)[C:42]([CH2:50][CH3:51])=[N:41]2)=[N:34]1

Participants

Conditions

Temperature: 87 °C

Procedure

To a suspension of imidazo[1,2-a]pyridine-3-carboxylic acid (45.1 mg, 0.278 mmol) in NMP (5 mL) was added 2,4,6-trichlorobenzoyl chloride (43.5 μL, 0.278 mmol) and triethylamine (38.8 μL, 0.278 mmol). The reaction mixture was stirred for 30 minutes. 1-((1,5-Dimethyl-1H-pyrazol-3-yl)methyl)-3-ethyl-1H-indazol-4-amine (50 mg, 0.186 mmol) was added to the reaction mixture, which was heated to 87° C. for 3 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, then concentrated under reduced pressure. The residue was triturated with Et2O to give final product (35 mg). MS (ES+APCI) m/z=414 (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-5c291f1084824f80a87d572847174367
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841455B2

Linked notes

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