1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 59726785, compound

HRID 906864Notes

Reaction equation

HRID 906864 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3](=O)[CH2:4][C:5]([C:7]1[CH:8]=[N:9][N:10]([C:12]2[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:15]=[CH:14][N:13]=2)[CH:11]=1)=O.[C:25]([CH2:27][C:28]([NH:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][C:33]=1[F:39])=[O:29])#[N:26].N12CCCN=C1CCCCC2>C1C=CC=CC=1>[F:39][C:33]1[CH:34]=[C:35]([F:38])[CH:36]=[CH:37][C:32]=1[CH2:31][N:30]1[C:5]([C:7]2[CH:8]=[N:9][N:10]([C:12]3[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:15]=[CH:14][N:13]=3)[CH:11]=2)=[CH:4][C:3]([C:2]([F:24])([F:23])[F:1])=[C:27]([C:25]#[N:26])[C:28]1=[O:29]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×HCID 2799809HCID 2799809, compoundHCID 86597534HCID 86597534, compound

Product 1

HCID 59726785HCID 59726785, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
90 °C

Procedure

4,4,4-Trifluoro-1-[1-(3-trifluoromethyl-pyridin-2-yl)-1H-pyrazol-4-yl]-butane-1,3-dione (143 mg, 0.41 mmol) and 2-cyano-N-(2,4-difluoro-benzyl)-acetamide (86 mg, 0.41 mmol) were suspended in 1.5 mL anhydrous benzene. To the above reaction mixture was added 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU (31 mg, 0.21 mmol). The mixture was heated at 90° C. under nitrogen atmosphere for overnight. After this period of time, the mixture was evaporated in vacuo and the resulting residue was purified by column chromatography on silica gel (35% EtOAC/Hexane) to give 1-(2,4-difluoro-benzyl)-2-oxo-4-trifluoromethyl-6-[1-(3-trifluoromethyl-pyridin-2-yl)-1H-pyrazol-4-yl]-1,2-dihydro-pyridine-3-carbonitrile as a yellow solid (78 mg, 36% yield). 1H-NMR (400 MHz, CDCl3): δ 5.42 (s, 2H), 6.61 (s, 1H), 6.82 (m, 1H), 6.89 (m, 1H), 7.12 (m, 1H), 7.58 (dd, 1H, J=4.80, J=8.08), 7.73 (s, 1H), 8.28 (dd, 1H, J=1.77, J=8.08), 8.32 (s, 1H), 8.72 (dd, 1H, J=1.77, J=4.80).

Workup

  1. waitAfter this period of time
  2. customthe mixture was evaporated in vacuo
  3. customthe resulting residue was purified by column chromatography on silica gel (35% EtOAC/Hexane)

Sources & evidence

ORD record
ord-66e35164702247cbba2eb9a42eee2806
Source dataset
uspto-grants-2011_09
Patent number
US08013001B2

Reaction notes

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