1,1'-Carbonyldiimidazole → HCID 178518660, compound

HRID 1622432Notes

Reaction equation

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

Participants

Conditions

Temperature: 20 °C

Procedure

3-(5-Morpholin-4-ylmethyl-1H-benzoimidazol-2-yl)-1H-pyrazol-4-ylamine (0.993 Kg, 3.33 mol, 1.O wt) and tetrahydrofuran (14.0 L, 15.0 vol) were charged to a flange flask equipped with a mechanical stirrer, condenser and thermometer. The contents were stirred under nitrogen at 15 to 25° C. and 1,1′-carbonyldiimidazole (0.596 Kg, 3.67 mol, o.óO wt) was added. The contents were then heated to 60 to 70° C. and stirred at this temperature for 16 to 24 hours. Reaction completion was determined by TLC analysis. The mixture was cooled to 15 to 20° C. and filtered. The filter-cake was washed with tetrahydrofuran (4.00 L, 4.O vol) and pulled dry for 15 to 30 minutes. The solid was dried under vacuum at 35 to 45° C. to yield 7-morpholin-4-ylmethyl-2,4-dihydro-1,2,4,5a,10-pentaaza-cyclopenta[a]fluoren-5-one (0.810 Kg, 75.0% th, 92.19% by HPLC area) as a purple solid.

Workup

customequipped with a mechanical stirrer, condenser
temperatureThe contents were then heated to 60 to 70° C.
stirringstirred at this temperature for 16 to 24 hours
customReaction completion
temperatureThe mixture was cooled to 15 to 20° C.
filtrationfiltered
washThe filter-cake was washed with tetrahydrofuran (4.00 L, 4.O vol)
custompulled dry for 15 to 30 minutes
customThe solid was dried under vacuum at 35 to 45° C.

Sources & evidence

ORD record: ord-b784ad33baa44dba9563f8fcc502bbd3
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778936B2

Reaction notes

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