1,4-Dioxane hydrochloride → (S)-N-(1-((6-cyclopropylpyridin-2-yl)methyl)-3-methyl-1H-indazol-4-yl)-7-(2-(3,4-dimethylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxamide Di-hydrochloride

HRID 706562Notes

Reaction equation

HRID 706562 reaction equation
[CH:1]1([C:4]2[N:9]=[C:8]([CH2:10][N:11]3[C:19]4[C:14](=[C:15]([NH:20][C:21]([C:23]5[N:27]6[CH:28]=[CH:29][C:30]([O:32][CH2:33][CH2:34][N:35]7[CH2:40][CH2:39][N:38]([CH3:41])[C@@H:37]([CH3:42])[CH2:36]7)=[CH:31][C:26]6=[N:25][CH:24]=5)=[O:22])[CH:16]=[CH:17][CH:18]=4)[C:13]([CH3:43])=[N:12]3)[CH:7]=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.[ClH:44].O1CCOCC1>C(Cl)Cl.CO>[ClH:44].[ClH:44].[CH:1]1([C:4]2[N:9]=[C:8]([CH2:10][N:11]3[C:19]4[C:14](=[C:15]([NH:20][C:21]([C:23]5[N:27]6[CH:28]=[CH:29][C:30]([O:32][CH2:33][CH2:34][N:35]7[CH2:40][CH2:39][N:38]([CH3:41])[C@@H:37]([CH3:42])[CH2:36]7)=[CH:31][C:26]6=[N:25][CH:24]=5)=[O:22])[CH:16]=[CH:17][CH:18]=4)[C:13]([CH3:43])=[N:12]3)[CH:7]=[CH:6][CH:5]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 57384859(S)-N-(1-((6-cyclopropylpyridin-2-yl)methyl)-3-methyl-1H-indazol-4-yl)-7-(2-(3,4-dimethylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxamide

Product 1

HCID 67977228(S)-N-(1-((6-cyclopropylpyridin-2-yl)methyl)-3-methyl-1H-indazol-4-yl)-7-(2-(3,4-dimethylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxamide Di-hydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

(S)—N-(1-((6-cyclopropylpyridin-2-yl)methyl)-3-methyl-1H-indazol-4-yl)-7-(2-(3,4-dimethylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxamide (81.6 mg, 0.141 mmol) was taken up in 2 mL of 4:1 DCM/MeOH-4M HCl/dioxane (0.071 mL, 0.282 mmol) was added and the mixture stirred at ambient temperature for one hour, then concentrated under reduced pressure and dried under vacuum for 16 hours to give 91.9 mgs (100%) of the HCl salt. [α]D=−3.6° (c=1.0, CHCl3).

Workup

  1. additionwas added
  2. concentrationconcentrated under reduced pressure
  3. customdried under vacuum for 16 hours

Sources & evidence

ORD record
ord-6d8a32c1d3c042e1bd2e728d380717b7
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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