O-Phenylenediamine → HCID 59852393, compound

HRID 2373172Notes

Reaction equation

HRID 2373172 reaction equation
[NH2:1][C:2]1[C:3]([C:15](O)=O)=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[CH:6][N:7]=1.[C:18]1([NH2:25])[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[NH2:24].C(P(=O)(OCC)OCC)#N.C(N(CC)CC)C>C(COC)OC.O>[NH:24]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:25]=[C:15]1[C:3]1[C:2]([NH2:1])=[N:7][CH:6]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)[N:4]=1

Participants

7

Reactant 4

HCID 7243O-PhenylenediamineHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 59852410HCID 59852410, compound

Product 1

HCID 59852393HCID 59852393, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
200 °C

Procedure

3-amino-6-(3-fluorophenyl)pyrazine-2 carboxylic acid (0.096 g, 0.41 mmol), ortho-phenylenediamine (0.049 g, 0.45 mmol), diethyl cyanophosphonate (0.07 g, 0.45 mmol), and triethylamine (0.083 g, 0.82 mmol) were combined in 5 mL of dimethoxyethane. The mixture was heated to 200° C. for 10 min in the SmithSynthesizer microwave. The cooled mixture was poured into 30 mL of H2O and the mixture was filtered to collect 3-(1H-benzimidazol-2-yl)-5-(3-fluorophenyl)pyrazin-2-amine (23 mg) as a yellow solid.

Workup

  1. filtrationthe mixture was filtered
  2. customto collect 3-(1H-benzimidazol-2-yl)-5-(3-fluorophenyl)pyrazin-2-amine (23 mg) as a yellow solid

Sources & evidence

ORD record
ord-c0f43f91feb54a418c1c18da6cc4e6c8
Source dataset
uspto-grants-2008_12
Patent number
US07459454B2

Reaction notes

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