Acetic Acid → HCID 67085298, compound

HRID 1484564Notes

Reaction equation

HRID 1484564 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]=O)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[C:12]([CH:14]=[C:15]([O-])[CH3:16])#[N:13].[Na+].[NH2:19][C:20]([C:24]([F:27])([F:26])[F:25])=[CH:21][C:22]#[N:23].C(O)(=O)C>C(O)CCCC.C1COCC1>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]3[C:21]([C:22]#[N:23])=[C:20]([C:24]([F:27])([F:26])[F:25])[NH:19][C:15]([CH3:16])=[C:14]3[C:12]#[N:13])=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 212506441H-Indazole-5-carboxaldehydeHCID 534010963-Amino-4,4,4-trifluorobut-2-enenitrileHCID 74083625Sodium 1-cyanoprop-1-en-2-olate

Product 1

HCID 67085298HCID 67085298, compound

Reagents, catalysts & solvents 2

HCID 62761-PentanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 250 mg (1.71 mmol) 1H-indazole-5-carbaldehyde, 180 mg (1.71 mmol) sodium 1-cyanoprop-1-en-2-olate and 931 mg (6.84 mmol) 3-amino-4,4,4-trifluorobut-2-enenitrile [preparation: A. W. Lutz, U.S. Pat. No. 3,635,977; C. G. Krespan, J. Org. Chem. 34, 42 (1969)] in 1-pentanol (2.5 ml) and acetic acid (0.15 ml) was heated to 105° C. overnight. After cooling, the reaction mixture was diluted with THF and directly purified by preparative RP-HPLC (acetonitrile/water+0.1% TFA gradient) yielding 131 mg (23% of th.) of the racemic title compound.

Workup

  1. custompreparation
  2. temperatureAfter cooling
  3. customdirectly purified by preparative RP-HPLC (acetonitrile/water+0.1% TFA gradient)

Sources & evidence

ORD record
ord-a12aa752af594cf4a7d7c35fb3121c5f
Source dataset
uspto-grants-2016_08
Patent number
US09422263B2

Reaction notes

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