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

HRID 706597Notes

Reaction equation

HRID 706597 reaction equation
F[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([NH:13][C:14]3[CH:22]=[CH:21][CH:20]=[C:19]4[C:15]=3[C:16]([CH3:31])=[N:17][N:18]4[CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[N:25]=3)=[O:12])=[CH:9][N:10]=[C:4]2[CH:3]=1.[NH:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1.[Cl:37]CCl>C(O)CCC>[ClH:37].[ClH:37].[CH3:31][C:16]1[C:15]2[C:19](=[CH:20][CH:21]=[CH:22][C:14]=2[NH:13][C:11]([C:8]2[N:5]3[CH:6]=[CH:7][C:2]([N:32]4[CH2:36][CH2:35][CH2:34][CH2:33]4)=[CH:3][C:4]3=[N:10][CH:9]=2)=[O:12])[N:18]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[N:25]=2)[N:17]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 31268PyrrolidineHCID 573866457-fluoro-N-(3-methyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

Product 1

HCID 67976036N-(3-methyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(pyrrolidin-1-yl)imidazo[1,2-a]pyridine-3-carboxamide dihydrochloride

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

7-Fluoro-N-(3-methyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (Example 53; 0.0144 g, 0.0347 mmol) was suspended in n-butanol (0.2 mL). To this was added pyrrolidine (7.25 μL, 0.0869 mmol) and the mixture was heated to 120° C. for 12 hours. The mixture was concentrated under reduced pressure and the resulting material was taken up in THF and concentrated three times to give a brown solid. This material was taken up in dichloromethane, washed with water and brine, dried over sodium sulfate and concentrated under reduced pressure (0.0127 g, 79%). The resulting material was treated with 2M HCl in diethyl ether to provide N-(3-methyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(pyrrolidin-1-yl)imidazo[1,2-a]pyridine-3-carboxamide dihydrochloride. MS (APCI), positive scan, m/z=466.3 (M+H).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. concentrationconcentrated three times
  3. customto give a brown solid
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure (0.0127 g, 79%)
  7. additionThe resulting material was treated with 2M HCl in diethyl ether

Sources & evidence

ORD record
ord-a4bfd483cc2e4aaea4f93a0eeeb42aec
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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