Choline bicarbonate → HCID 178428548, compound

HRID 1484572Notes

Reaction equation

HRID 1484572 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 178428546HCID 178428546, compound

Product 1

HCID 178428548HCID 178428548, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 101 mg (0.30 mmol) (4S)-2-methyl-4-(3-methyl-1H-indazol-5-yl)-6-(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarbonitrile (Example 6) in ethanol (2.43 ml) under argon atmosphere was added 52 μl (0.30 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 7 days and then centrifuged to yield 70 mg (51% 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 7 days

Sources & evidence

ORD record
ord-a550c311412f45909fac535e1280042e
Source dataset
uspto-grants-2016_08
Patent number
US09422263B2

Reaction notes

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