HCID 90010296, compound → HCID 136273996, compound

HRID 706785Notes

Reaction equation

HRID 706785 reaction equation
[CH3:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][N:9]2[CH:13]=[CH:12][CH:11]=[C:10]2[C:14]([NH2:16])=[O:15])=O)=[CH:4][CH:3]=1>N>[C:2]1([CH3:1])[CH:18]=[CH:17][C:5]([C:6]2[NH:16][C:14](=[O:15])[C:10]3=[CH:11][CH:12]=[CH:13][N:9]3[N:8]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 90010296HCID 90010296, compound

Product 1

HCID 136273996HCID 136273996, compound

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 1-(4-methyl-benzoylamino)-1H-pyrrole-2-carboxylic acid amide (111 mg, 0.457 mmol) in 25% aqueous ammonia solution (0.7 ml) is heated to 100° C. in a closed reaction vial and stirred at this temperature for 40 hours. The reaction mixture is allowed to cool to room temperature and purged with nitrogen. Aqueous 1 N hydrochloric is added to reach a pH value of 2. The solids are filtered off and washed with water. Chromatography on a silica gel column with methanol/dichloromethane as eluent affords 2-p-tolyl-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one as white crystals; HPLC/MS 2.45 min (B), [M+H] 226;

Workup

  1. temperatureto cool to room temperature
  2. custompurged with nitrogen
  3. additionAqueous 1 N hydrochloric is added
  4. filtrationThe solids are filtered off
  5. washwashed with water

Sources & evidence

ORD record
ord-bf3cab9f4d32428cbe9a8ef3221fa6bd
Source dataset
uspto-grants-2015_11
Patent number
US09174995B2

Reaction notes

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