Diisopropylethylamine → 7-fluoro-N-(3-methyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 706596Notes

Reaction equation

HRID 706596 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([OH:13])=O)=[CH:9][N:10]=[C:4]2[CH:3]=1.[CH3:14][C:15]1[C:23]2[C:22]([NH2:24])=[CH:21][CH:20]=[CH:19][C:18]=2[N:17]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[N:27]=2)[N:16]=1.C(N(C(C)C)CC)(C)C>S(Cl)(Cl)=O.CN(C=O)C.O>[F:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([NH:24][C:22]3[CH:21]=[CH:20][CH:19]=[C:18]4[C:23]=3[C:15]([CH3:14])=[N:16][N:17]4[CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[N:27]=3)=[O:13])=[CH:9][N:10]=[C:4]2[CH:3]=1

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 672607377-Fluoroimidazo[1,2-a]pyridine-3-carboxylic acidHCID 672609383-methyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-amine

Product 1

HCID 573866457-fluoro-N-(3-methyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamideYield 54%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 24386Thionyl ChlorideSolvent

Procedure

7-Fluoroimidazo[1,2-a]pyridine-3-carboxylic acid (0.081 g, 0.449 mmol) was dissolved in thionyl chloride (2 mL). To this was added a few drops of DMF and the mixture stirred at ambient temperature for 1 hour. The mixture was concentrated under reduced pressure and the resulting solid was dissolved in 3 mL of 1:2 DCM:DMF. To this was added 3-methyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-amine (0.114 g, 0.451 mmol) followed by diisopropylethylamine (235 μL, 1.35 mmol). This mixture was stirred at ambient temperature for 2 hours, then diluted with water (22 mL), forming a beige precipitate with stirring for several hours. The solids were collected to give 0.100 g (54%) of the title compound. MS (APCI), positive scan, m/z=415.2 (M+H).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionthe resulting solid was dissolved in 3 mL of 1:2 DCM
  3. stirringThis mixture was stirred at ambient temperature for 2 hours
  4. customforming a beige precipitate
  5. stirringwith stirring for several hours
  6. customThe solids were collected

Sources & evidence

ORD record
ord-36fd808036d5410a918c9f126b76eedd
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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