HCID 57828608, compound → HCID 52938809, compound

HRID 1910668Notes

Reaction equation

HRID 1910668 reaction equation
[C:1]([C:3]([C:23](=O)[CH3:24])=[CH:4][C:5]1[O:13][C:12]2[CH:11]=[CH:10][N:9]=[C:8]([NH:14][C:15](=[O:22])[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:7]=2[CH:6]=1)#[N:2].[NH2:26]/[C:27](/[C:31]([F:34])([F:33])[F:32])=[CH:28]/[C:29]#[N:30]>CC(O)C>[C:1]([C:3]1[CH:4]([C:5]2[O:13][C:12]3[CH:11]=[CH:10][N:9]=[C:8]([NH:14][C:15](=[O:22])[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:7]=3[CH:6]=2)[C:28]([C:29]#[N:30])=[C:27]([C:31]([F:34])([F:33])[F:32])[NH:26][C:23]=1[CH3:24])#[N:2]

Participants

4

Reactant 2

HCID 57828608HCID 57828608, compoundHCID 67154537N-{2-(2-Cyano-3-oxobut-1-en-1-yl)furo[3,2-c]pyridin-4-yl}benzamide

Product 1

HCID 52938809HCID 52938809, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 200 mg (0.604 mmol) N-{2-(2-cyano-3-oxobut-1-en-1-yl)furo[3,2-c]pyridin-4-yl}-benzamide (Example 4A) and 329 mg (2.41 mmol) (2E)-3-amino-4,4,4-trifluorobut-2-enenitrile [CAS Reg.-No. 33561-24-9; prepared following A. W. Lutz, U.S. Pat. No. 3,635,977 and also C. G. Krespan, J. Org. Chem. 34, 42-45 (1969)] in 2-propanol (1 ml) was stirred at reflux for 12 h. Upon cooling, the mixture was concentrated under reduced pressure, and the residue was directly purified by preparative RP-HPLC (acetonitrile/water+0.1% TFA gradient, final mixture 90:10 v/v) to yield 171 mg (63% of th.) of the racemic title compound.

Workup

  1. customprepared following A
  2. temperatureat reflux for 12 h
  3. temperatureUpon cooling
  4. concentrationthe mixture was concentrated under reduced pressure
  5. customthe residue was directly purified by preparative RP-HPLC (acetonitrile/water+0.1% TFA gradient, final mixture 90:10 v/v)

Sources & evidence

ORD record
ord-062570074b15442cbcd082446158e474
Source dataset
uspto-grants-2013_12
Patent number
US08604028B2

Reaction notes

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