Choline bicarbonate → HCID 178428421, compound

HRID 1484570Notes

Reaction equation

HRID 1484570 reaction equation
[F:1][CH:2]([F:24])[C:3]1[NH:4][C:5]([CH3:23])=[C:6]([C:21]#[N:22])[CH:7]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][N:15]=[C:14]3[CH3:20])[C:8]=1[C:9]#[N:10].C(=O)([O-])O.[OH:29][CH2:30][CH2:31][N+:32]([CH3:35])([CH3:34])[CH3:33]>C(O)C>[C:21]([C:6]1[CH:7]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][N:15]=[C:14]3[CH3:20])[C:8]([C:9]#[N:10])=[C:3]([CH:2]([F:1])[F:24])[N-:4][C:5]=1[CH3:23])#[N:22].[OH:29][CH2:30][CH2:31][N+:32]([CH3:35])([CH3:34])[CH3:33]

Participants

4

Reactant 2

HCID 6552Choline bicarbonateHCID 178428420HCID 178428420, compound

Product 1

HCID 178428421HCID 178428421, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 75 mg (0.23 mmol) 2-(difluoromethyl)-6-methyl-4-(3-methyl-1H-indazol-5-yl)-1,4-dihydropyridine-3,5-dicarbonitrile (Enantiomer 1; Example 2) in ethanol (1.6 ml) under argon atmosphere was added 32.6 μl (0.23 mmol) 2-hydroxy-N,N,N-trimethylethanaminium hydrogencarbonate solution (choline bicarbonate, 80% in water), and the mixture was stirred at reflux temperature for 1 h. Subsequently, the solution was evaporated, and the residue was dried in vacuo. The precipitate was stirred in 1.5 ml THF for 3 days and then centrifuged to yield 56 mg (56% of th.) of the title compound as a yellow solid.

Workup

  1. temperatureat reflux temperature for 1 h
  2. customSubsequently, the solution was evaporated
  3. customthe residue was dried in vacuo
  4. stirringThe precipitate was stirred in 1.5 ml THF for 3 days

Sources & evidence

ORD record
ord-2981111f8a274cceb9126d7437312c8e
Source dataset
uspto-grants-2016_08
Patent number
US09422263B2

Reaction notes

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