1,1'-Carbonyldiimidazole → 7,8-Dihydro-8-(3-(trifluoromethyl)phenyl)-3H,6H-1,4,5a,8a-tetraazaacenaphthylene-3,5(4H)-dione

HRID 2050510Notes

Reaction equation

HRID 2050510 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([CH:9]2[N:14]3[N:15]=[CH:16][C:17]([C:18]([NH2:20])=[O:19])=[C:13]3[NH:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.[C:23](N1C=CN=C1)(N1C=CN=C1)=[O:24]>O1CCCC1>[F:22][C:2]([F:21])([F:1])[C:3]1[CH:4]=[C:5]([CH:9]2[N:14]3[C:13]4[N:12]([C:23](=[O:24])[NH:20][C:18](=[O:19])[C:17]=4[CH:16]=[N:15]3)[CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 1356213974,5,6,7-Tetrahydro-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide

Product 1

HCID 200583797,8-Dihydro-8-(3-(trifluoromethyl)phenyl)-3H,6H-1,4,5a,8a-tetraazaacenaphthylene-3,5(4H)-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 3.0 g portion of 4,5,6,7-tetrahydro-7-(3-(trifluoromethyl)phenyl)pyrazolo(1,5-a)pyrimidine-3-carboxamide (Example 13) suspended in 40 ml of dry tetrahydrofuran is added portionwise under nitrogen 8.0 g of 1,1'-carbonyldiimidazole and 60 ml of dry tetrahydrofuran. The reaction mixture is heated at reflux for 96 hours, and then is cooled to give a white precipitate which is collected by filtration. The precipitate is treated with 10 ml of water, filtered and dried to give 1.05 g of the desired product as a white solid, mp 297-300° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 96 hours
  3. temperatureis cooled
  4. customto give a white precipitate which
  5. filtrationis collected by filtration
  6. additionThe precipitate is treated with 10 ml of water
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-9331bca5e0634efbbe301c0792976ec7
Source dataset
uspto-grants-1991_05
Patent number
US05013737

Reaction notes

Loading…