Choline bicarbonate → HCID 178428547, compound

HRID 1484575Notes

Reaction equation

HRID 1484575 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([C:22]([F:25])([F:24])[F:23])=[C:5]([C:20]#[N:21])[C@H:6]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][N:14]=[C:13]3[CH3:19])[C:7]=1[C:8]#[N:9].C(=O)([O-])O.[OH:30][CH2:31][CH2:32][N+:33]([CH3:36])([CH3:35])[CH3:34]>C(O)C>[C:8]([C:7]1[C@@H:6]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][N:14]=[C:13]3[CH3:19])[C:5]([C:20]#[N:21])=[C:4]([C:22]([F:23])([F:25])[F:24])[N-:3][C:2]=1[CH3:1])#[N:9].[OH:30][CH2:31][CH2:32][N+:33]([CH3:36])([CH3:35])[CH3:34]

Participants

4

Reactant 2

HCID 6552Choline bicarbonateHCID 178428545HCID 178428545, compound

Product 1

HCID 178428547HCID 178428547, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 100 mg (0.29 mmol) (4R)-2-methyl-4-(3-methyl-1H-indazol-5-yl)-6-(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarbonitrile (Example 5) in ethanol (2.1 ml) under argon atmosphere was added 41 μl (0.29 mmol) 2-hydroxy-N,N,N-trimethylethanaminium hydrogencarbonate solution (choline bicarbonate, 80% in water), and the mixture was stirred at reflux temperature for 40 min. Subsequently, the solution was evaporated, and the residue was dried in vacuo. The precipitate was stirred in 1.5 ml THF/pentane (9:1 v/v) for 3 days and then centrifuged to yield 84 mg (64% of th.) of the title compound as a solid.

Workup

  1. temperatureat reflux temperature for 40 min
  2. customSubsequently, the solution was evaporated
  3. customthe residue was dried in vacuo
  4. stirringThe precipitate was stirred in 1.5 ml THF/pentane (9:1 v/v) for 3 days

Sources & evidence

ORD record
ord-c647722a08124727baaa56b0a9a4f56d
Source dataset
uspto-grants-2016_08
Patent number
US09422263B2

Reaction notes

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