2-Amino-4-(3-methoxyphenyl)-1H-pyrrole-3-carbonitrile → HCID 18792871, compound

HRID 1004605Notes

Reaction equation

HRID 1004605 reaction equation
[C:1]([C:3]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=2)=[CH:6][NH:5][C:4]=1[NH:16][CH:17]=[NH:18])#[N:2].NC1NC=C(C2C=CC=C(OC)C=2)C=1C#N>C(OCC)(OCC)OCC>[CH3:15][O:14][C:10]1[CH:9]=[C:8]([C:7]2[C:3]3[C:1]([NH2:2])=[N:18][CH:17]=[N:16][C:4]=3[NH:5][CH:6]=2)[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 187929202-Amino-4-(3-methoxyphenyl)-1H-pyrrole-3-carbonitrileHCID 178489845HCID 178489845, compound

Product 1

HCID 18792871HCID 18792871, compound

Reagents, catalysts & solvents 1

HCID 31214Ethyl orthoformateSolvent

Conditions

Temperature
140 °C

Procedure

N-[3-Cyano-4-(3-methoxy-phenyl)-1H-pyrrol-2-yl]formamidine: 5.30 g of 2-amino4-(3-methoxy-phenyl)-1H-pyrrole-3-carbonitrile are dissolved in 50 ml of triethyl orthoformate, and the solution is stirred for 1 hour at 140° C. The triethyl orthoformate is removed under a high vacuum and the residue is dissolved in methanol saturated with ammonia. Stirring is carried out for 20 hours at room temperature, followed by filtration. The product is recrystallised from ethanol. M.p.: 188-190° C.

Workup

  1. customThe triethyl orthoformate is removed under a high vacuum
  2. dissolutionthe residue is dissolved in methanol saturated with ammonia
  3. stirringStirring
  4. waitis carried out for 20 hours at room temperature
  5. filtrationfollowed by filtration
  6. customThe product is recrystallised from ethanol

Sources & evidence

ORD record
ord-85c73a0a5b7743778a37065400de14ab
Source dataset
uspto-grants-2000_04
Patent number
US06051577

Reaction notes

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