Triethylamine → N-(2-aminopyrimidin-5-yl)-2-methyl-5-(3-(trifluoromethyl)phenylsulfonamido)benzamide

HRID 453363Notes

Reaction equation

HRID 453363 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:18])=[C:6]([CH:17]=1)[C:7]([NH:9][C:10]1[CH:11]=[N:12][C:13]([NH2:16])=[N:14][CH:15]=1)=[O:8].C(N(CC)CC)C.[F:26][C:27]([F:39])([F:38])[C:28]1[CH:29]=[C:30]([S:34](Cl)(=[O:36])=[O:35])[CH:31]=[CH:32][CH:33]=1>C(Cl)(Cl)Cl>[NH2:16][C:13]1[N:12]=[CH:11][C:10]([NH:9][C:7](=[O:8])[C:6]2[CH:17]=[C:2]([NH:1][S:34]([C:30]3[CH:31]=[CH:32][CH:33]=[C:28]([C:27]([F:26])([F:38])[F:39])[CH:29]=3)(=[O:36])=[O:35])[CH:3]=[CH:4][C:5]=2[CH3:18])=[CH:15][N:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27332503-(Trifluoromethyl)benzenesulfonyl chlorideHCID 161168485-amino-N-(2-aminopyrimidin-5-yl)-2-methylbenzamide

Product 1

HCID 16118872N-(2-aminopyrimidin-5-yl)-2-methyl-5-(3-(trifluoromethyl)phenylsulfonamido)benzamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 5-amino-N-(2-aminopyrimidin-5-yl)-2-methylbenzamide 28 (85 mg, 0.349 mmol) in CHCl3 (2 mL) was added triethylamine (0.453 mmol) and 3-(trifluoromethyl)benzene-1-sulfonyl chloride (0.064 mL, 0.401 mmol). The reaction mixture was heated to reflux for 12 h, cooled to rt and concentrated in vacuo. The crude residue was adsorbed on SiO2 and purified by flash chromatography (CH2Cl2/MeOH 99:1) on SiO2 to afford N-(2-aminopyrimidin-5-yl)-2-methyl-5-(3-(trifluoromethyl)phenylsulfonamido)benzamide 29. MS m/z found 452 [MH+]; calc. for C19H16F3N5O3S=451.09.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 12 h
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography (CH2Cl2/MeOH 99:1) on SiO2

Sources & evidence

ORD record
ord-9b430f712520417784015e9c854715ff
Source dataset
uspto-grants-2013_07
Patent number
US08492404B2

Reaction notes

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