Water → HCID 59376777, compound

HRID 1771866Notes

Reaction equation

HRID 1771866 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C([C:14]1[C:15](/[N:23]=[CH:24]/[N:25]([CH3:27])C)=[N:16][C:17]([CH:20]([CH3:22])[CH3:21])=[CH:18][CH:19]=1)#N.O>C(O)(=O)C>[CH:20]([C:17]1[CH:18]=[CH:19][C:14]2[C:27]([NH:1][C:2]3[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=3)[C:5]([O:7][CH3:8])=[O:6])=[N:25][CH:24]=[N:23][C:15]=2[N:16]=1)([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 962WaterHCID 78274Benzoic acid, 3-amino-, methyl esterHCID 71307731HCID 71307731, compound

Product 1

HCID 59376777HCID 59376777, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

To methyl 3-aminobenzoate (0.50 g, 3.31 mmol) in acetic acid (10 mL) was added (E)-N′-(3-cyano-6-isopropylpyridin-2-yl)-N,N-dimethylformimidamide (0.71 g, 3.31 mmol) and the mixture was stirred at 120° C. for 25 minutes. Reaction mixture was cooled to room temperature and a solid formed. Water was added and solid was collected by filtration. Purification by chromatography on silica gel eluting with 0-30% methanol in dichloromethane gave the title compound (1.05 g, 98% yield).

Workup

  1. customReaction mixture
  2. temperaturewas cooled to room temperature
  3. customa solid formed
  4. filtrationsolid was collected by filtration
  5. customPurification by chromatography on silica gel eluting with 0-30% methanol in dichloromethane

Sources & evidence

ORD record
ord-1e603d41edd04c20ab228f286ccdbce6
Source dataset
uspto-grants-2016_02
Patent number
US09249138B2

Reaction notes

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