5-[(4-Fluorophenyl)methyl]-4H-1,2,4-triazole-3,4-diamine → 5-Chloro-3-(4-fluoro-benzyl)-9H-1,2,3a,4,9,10-hexaaza-cyclopenta[b]fluoren-6-ol

HRID 1822908Notes

Reaction equation

HRID 1822908 reaction equation
[Cl:1][C:2]1[C:10]([OH:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=O)[C:5](=O)[NH:6]2.[F:14][C:15]1[CH:28]=[CH:27][C:18]([CH2:19][C:20]2[N:21]([NH2:26])[C:22]([NH2:25])=[N:23][N:24]=2)=[CH:17][CH:16]=1>C(O)CO>[Cl:1][C:2]1[C:10]([OH:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]1[C:5]([NH:6]2)=[N:25][C:22]2=[N:23][N:24]=[C:20]([CH2:19][C:18]3[CH:27]=[CH:28][C:15]([F:14])=[CH:16][CH:17]=3)[N:21]2[N:26]=1

Participants

4

Reactant 2

HCID 219193225-[(4-Fluorophenyl)methyl]-4H-1,2,4-triazole-3,4-diamineHCID 221696644-chloro-5-hydroxy-1H-indole-2,3-dione

Product 1

HCID 1355026905-Chloro-3-(4-fluoro-benzyl)-9H-1,2,3a,4,9,10-hexaaza-cyclopenta[b]fluoren-6-ol

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
125 °C

Procedure

According to a cyclization procedure for Example 30, 0.60 mmol of 4-chloro-5-hydroxy-1H-indole-2,3-dione (118.5 mg) and 0.70 mmol of (4-fluoro-benzyl)-[1,2,4]triazole-3,4-diamine (145 mg) in 2 mL of ethylene glycol was stirred at 125° C. overnight (16 hr).

Sources & evidence

ORD record
ord-c6138ec3d0b34960abf1beb7d25097e7
Source dataset
uspto-grants-2006_05
Patent number
US07037909B2

Reaction notes

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