2-chloro-N,N-dimethylacetamide → HCID 70945201, compound

HRID 517976Notes

Reaction equation

HRID 517976 reaction equation
FC(F)(F)C(O)=O.[CH3:8][N:9]1[C:17]2[CH:16]=[C:15]([C:18]3[CH:19]=[N:20][C:21]([O:28][CH2:29][CH2:30][CH:31]4[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]4)=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=3)[N:14]=[C:13]([C:37]#[N:38])[C:12]=2[N:11]=[N:10]1.C(N(CC)C(C)C)(C)C.[Cl:48][CH2:49][C:50]([N:52]([CH3:54])[CH3:53])=[O:51]>C(#N)C>[ClH:48].[CH3:8][N:9]1[C:17]2[CH:16]=[C:15]([C:18]3[CH:19]=[N:20][C:21]([O:28][CH2:29][CH2:30][CH:31]4[CH2:36][CH2:35][N:34]([CH2:49][C:50]([N:52]([CH3:54])[CH3:53])=[O:51])[CH2:33][CH2:32]4)=[C:22]([C:24]([F:25])([F:26])[F:27])[CH:23]=3)[N:14]=[C:13]([C:37]#[N:38])[C:12]=2[N:11]=[N:10]1

Participants

5

Reactant 3

HCID 758862-chloro-N,N-dimethylacetamideHCID 81531DiisopropylethylamineHCID 866733511-methyl-6-(6-(2-(piperidin-4-yl)ethoxy)-5-(trifluoromethyl)pyridin-3-yl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile trifluoroacetate

Product 1

HCID 70945201HCID 70945201, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 1-methyl-6-(6-(2-(piperidin-4-yl)ethoxy)-5-(trifluoromethyl)-pyridin-3-yl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile trifluoroacetate (200 mg) and N,N-diisopropylethylamine (310 μl) in acetonitrile (8 ml), 2-chloro-N,N-dimethylacetamide (77 μl, 91 mg) was added and the mixture stirred at 20° C. for 65 h. The reaction mixture was concentrated. The residue diluted with water (20 ml) and extrated with DCM (50 ml×3), combined DCM layer dried over sodium sulphate and solvent removed under reduced pressure. The residue was then purified by Strata Si column (5 g, dichloromethane:methanol=1:0, 25:1 to 15:1), converted to hydrochloric acid salt using 2N hydrochloric acid in diethyl ether to give 1-methyl-6-(6-(2-(1-(2-dimethylamino-2-oxo-ethyl)piperidin-4-yl)ethoxy)-5-(trifluoromethyl)pyridin-3-yl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile hydrochloride (179 mg).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionThe residue diluted with water (20 ml)
  3. dry with materialdried over sodium sulphate and solvent
  4. customremoved under reduced pressure
  5. customThe residue was then purified by Strata Si column (5 g, dichloromethane:methanol=1:0, 25:1 to 15:1)

Sources & evidence

ORD record
ord-e04a2a945f564b1db4571999ca5d01d3
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

Loading…