Triethylamine → HCID 67260151, compound

HRID 79465Notes

Reaction equation

HRID 79465 reaction equation
[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][C:22]([CH2:24][CH2:25][CH2:26]O)=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([CH3:35])[N:30]=2)[N:4]=1)[CH3:2].C(N(CC)CC)C.CS(Cl)(=O)=O.[CH3:48][N:49]1[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]1>O1CCCC1>[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][C:22]([CH2:24][CH2:25][CH2:26][N:52]4[CH2:53][CH2:54][N:49]([CH3:48])[CH2:50][CH2:51]4)=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([CH3:35])[N:30]=2)[N:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 531671-MethylpiperazineHCID 67261118HCID 67261118, compound

Product 1

HCID 67260151HCID 67260151, compoundYield 11.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(3-Ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(3-hydroxypropyl)imidazo[1,2-a]pyridine-3-carboxamide (77 mg, 0.16 mmol) was dissolved in tetrahydrofuran (0.8 mL) and treated with triethylamine (66 μL, 0.48 mmol) followed by dropwise addition of methanesulfonyl chloride (38 mL, 0.49 mmol). The mixture was stirred at ambient temperature for 2.5 hours. 1-Methyl piperazine (365 μL, 3.3 mmol) was added and the mixture was heated to 60° C. for 10 hours. The mixture was quenched with the addition of saturated sodium bicarbonate solution and extracted with dichloromethane 3 times. The combined extracts were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified using preparative thin layer chromatography (silica, 2 mm) eluting with 10% methanol/dichloromethane with 0.2% ammonium hydroxide to give N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(3-(4-methylpiperazin-1-yl)propyl) imidazo[1,2-a]pyridine-3-carboxamide (10 mg). MS m/z 551.4 (M+1, APCI+).

Workup

  1. temperaturethe mixture was heated to 60° C. for 10 hours
  2. customThe mixture was quenched with the addition of saturated sodium bicarbonate solution
  3. extractionextracted with dichloromethane 3 times
  4. dry with materialThe combined extracts were dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified
  7. washeluting with 10% methanol/dichloromethane with 0.2% ammonium hydroxide

Sources & evidence

ORD record
ord-783a9b18fe024caa8e38ab3f4ae810b7
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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