5-[(4-Fluorophenyl)methyl]-4H-1,2,4-triazole-3,4-diamine → Diethyl-{2-[3-(4-fluoro-benzyl)-5,8-dimethyl-9H-1,2,3a,4,9,10-hexaaza-cyclopenta[b]fluoren-6-yl]-ethyl}-amine hydrochloride

HRID 1822912Notes

Reaction equation

HRID 1822912 reaction equation
[ClH:1].C(N([CH:7]([C:9]1[C:10]([CH3:21])=[C:11]2[C:15](=[C:16]([CH3:18])[CH:17]=1)[NH:14][C:13](=O)[C:12]2=O)[CH3:8])CC)C.[F:22][C:23]1[CH:36]=[CH:35][C:26]([CH2:27][C:28]2[N:29]([NH2:34])[C:30]([NH2:33])=[N:31][N:32]=2)=[CH:25][CH:24]=1>C(O)CO.O.C(NCC)C>[ClH:1].[CH2:13]([N:14]([CH2:15][CH3:11])[CH2:8][CH2:7][C:9]1[C:10]([CH3:21])=[C:11]2[C:15](=[C:16]([CH3:18])[CH:17]=1)[NH:14][C:13]1[C:12]2=[N:34][N:29]2[C:28]([CH2:27][C:26]3[CH:35]=[CH:36][C:23]([F:22])=[CH:24][CH:25]=3)=[N:32][N:31]=[C:30]2[N:33]=1)[CH3:12]

Participants

6

Reactant 2

HCID 219193225-[(4-Fluorophenyl)methyl]-4H-1,2,4-triazole-3,4-diamineHCID 695972035-(N,N-diethylamino-2-ethyl)-4,7-dimethyl-1H-indole-2,3-dione hydrochloride

Product 1

HCID 135788272Diethyl-{2-[3-(4-fluoro-benzyl)-5,8-dimethyl-9H-1,2,3a,4,9,10-hexaaza-cyclopenta[b]fluoren-6-yl]-ethyl}-amine hydrochloride

Reagents, catalysts & solvents 3

HCID 174Ethylene GlycolSolventHCID 962WaterSolventHCID 8021DiethylamineSolvent

Procedure

0.60 mmol of 5-(N,N-diethylamino-2-ethyl)-4,7-dimethyl-1H-indole-2,3-dione hydrochloride (186.5 mg) and 0.70 mmol of (4-fluoro-benzyl)-[1,2,4]triazole-3,4-diamine (145 mg) in 1.5 mL of ethylene glycol was stirred at 125° C. for 1 day. The mixture was cooled to room temperature, diluted with water (5 mL), and neat diethylamine 0.5 mL was added. Stirred for 3 hours, the precipitate was collected by filtration, washed with water and dried on highvac. The obtained free base was suspended in water (10 mL), 2M HCl 0.5 mL was added, heated to boil, sonicated briefly while hot and then allowed to crystallize in a refrigerator (+5° C.) overnight. The precipitate was collected by filtration, washed with ice-cold water (2×1 mL) and dried on high vacuum.

Workup

  1. additionwas added
  2. filtrationthe precipitate was collected by filtration
  3. washwashed with water
  4. customdried on highvac
  5. addition2M HCl 0.5 mL was added
  6. temperatureheated
  7. customsonicated briefly while hot and
  8. customto crystallize in a refrigerator (+5° C.) overnight
  9. filtrationThe precipitate was collected by filtration
  10. washwashed with ice-cold water (2×1 mL)
  11. customdried on high vacuum

Sources & evidence

ORD record
ord-745b65eade0c4455b130bc24b587b23e
Source dataset
uspto-grants-2006_05
Patent number
US07037909B2

Reaction notes

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