Choline bicarbonate → HCID 178483581, compound

HRID 1484580Notes

Reaction equation

HRID 1484580 reaction equation
[F:1][CH:2]([F:26])[C:3]1[NH:4][C:5]([CH:23]([F:25])[F:24])=[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:31][CH2:32][CH2:33][N+:34]([CH3:37])([CH3:36])[CH3:35].C1COCC1>C(O)C>[C:9]([C:8]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:6]([C:21]#[N:22])=[C:5]([CH:23]([F:24])[F:25])[N-:4][C:3]=1[CH:2]([F:1])[F:26])#[N:10].[OH:31][CH2:32][CH2:33][N+:34]([CH3:37])([CH3:36])[CH3:35]

Participants

5

Reactant 3

HCID 6552Choline bicarbonateHCID 8028TetrahydrofuranHCID 178434239HCID 178434239, compound

Product 1

HCID 178483581HCID 178483581, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 80 mg (0.22 mmol) 2,6-bis(difluoromethyl)-4-(3-methyl-1H-indazol-5-yl)-1,4-dihydropyridine-3,5-dicarbonitrile (Example 13) in ethanol (1.52 ml) under argon atmosphere was added 31 μl (0.22 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, a weak argon stream was led over the solution mixture. The crude product was treated with THF (1.5 ml) and stirred for 2 days under argon. The resulting precipitate was collected by centrifugation and dried in vacuo to yield 57 mg (54% of th.) of the title compound as a yellow solid.

Workup

  1. temperatureat reflux temperature for 1 h
  2. stirringstirred for 2 days under argon
  3. customThe resulting precipitate was collected by centrifugation
  4. customdried in vacuo

Sources & evidence

ORD record
ord-dbf8ec7ef3e24df9a6bc9a6d2c5a56bf
Source dataset
uspto-grants-2016_08
Patent number
US09422263B2

Reaction notes

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