Benzamide, 3-amino-4-methoxy- → HCID 90102876, compound

HRID 1052448Notes

Reaction equation

HRID 1052448 reaction equation
[Cl:1][C:2]1[C:7]([C:8](Cl)=[O:9])=[C:6]([Cl:11])[N:5]=[CH:4][N:3]=1.[NH2:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[C:16]([NH2:18])=[O:17]>ClCCl>[C:16]([C:15]1[CH:19]=[CH:20][C:21]([O:22][CH3:23])=[C:13]([NH:12][C:8]([C:7]2[C:6]([Cl:11])=[N:5][CH:4]=[N:3][C:2]=2[Cl:1])=[O:9])[CH:14]=1)(=[O:17])[NH2:18]

Participants

4

Reactant 2

HCID 87135Benzamide, 3-amino-4-methoxy-HCID 121633604,6-Dichloro-pyrimidine-5-carbonyl chloride

Product 1

HCID 90102876HCID 90102876, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

4,6-Dichloropyrimidine-5-carbonyl chloride (430 mg, 2.03 mmol, prepared according to E. V. Tarasov et al. Synlett 2000, 5, 625-626) was dissolved in dichloromethane (3 ml) and TEA (283 μl, 2.03 mmol) was added. To this solution, 3-amino-4-methoxybenzamide (338 mg, 2.03 mmol) dissolved in 3 ml dichloromethane was added dropwise and the mixture was stirred for 60 min. The reaction mixture was then diluted with dichloromethane, washed with 4% sodium bicarbonate solution, dried over magnesium sulphate, filtered and evaporated. The crude (366 mg, 93% purity, 66% yield) was used in the next synthetic step without further purification.

Workup

  1. additionwas added dropwise
  2. washwashed with 4% sodium bicarbonate solution
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude (366 mg, 93% purity, 66% yield) was used in the next synthetic step without further purification

Sources & evidence

ORD record
ord-3da7c793d6c8474f9037f7167699b7f0
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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