4-[(4,5-Diamino-4H-1,2,4-triazol-3-yl)methyl]phenol → 5-Chloro-3-(4-hydroxy-benzyl)-9H-1,2,3a,4,9,10-hexaaza-cyclopenta[b]fluoren-6-ol

HRID 1822909Notes

Reaction equation

HRID 1822909 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.[NH2:14][N:15]1[C:19]([NH2:20])=[N:18][N:17]=[C:16]1[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=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:20][C:19]2=[N:18][N:17]=[C:16]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=3)[N:15]2[N:14]=1

Participants

4

Reactant 2

HCID 219193134-[(4,5-Diamino-4H-1,2,4-triazol-3-yl)methyl]phenolHCID 221696644-chloro-5-hydroxy-1H-indole-2,3-dione

Product 1

HCID 1354578465-Chloro-3-(4-hydroxy-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-(4,5-diamino-4H-[1,2,4]triazol-3-ylmethyl)-phenol (144 mg) in 2 mL of ethylene glycol was stirred at 125° C. overnight (16 hr).

Sources & evidence

ORD record
ord-df82bac2a79840c5b385edefbf7ce618
Source dataset
uspto-grants-2006_05
Patent number
US07037909B2

Reaction notes

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