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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
Notes
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Reaction equation

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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 73142Imidazo(1,2-a)pyridine-3-carboxylic acidHCID 27337032,4,6-Trichlorobenzoyl chlorideHCID 672600441-((1,5-dimethyl-1H-pyrazol-3-yl)methyl)-3-ethyl-1H-indazol-4-amine

Product 1

HCID 67260401N-(1-((1,5-dimethyl-1H-pyrazol-3-yl)methyl)-3-ethyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide
Yield 45.5%

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolventHCID 14798Sodium HydroxideSolvent

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

  1. temperatureThe mixture was cooled to ambient temperature
  2. washThe organic phase was washed with water and brine
  3. concentrationconcentrated under reduced pressure
  4. 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

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes