p-Toluenesulfonic acid → HCID 53237606, compound

HRID 1966713Notes

Reaction equation

HRID 1966713 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([NH2:19])[C:11]([NH:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:12][CH:13]=2)=[CH:4][N:3]=1.[Cl:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=O)=[C:23]([N:29]2[CH:33]=[N:32][CH:31]=[N:30]2)[CH:22]=1.CC1C=CC(S(O)(=O)=O)=CC=1>CO>[C:15]([N:14]1[C:11]2[CH:12]=[CH:13][C:8]([C:5]3[CH:4]=[N:3][C:2]([NH2:1])=[N:7][CH:6]=3)=[CH:9][C:10]=2[N:19]=[C:25]1[C:24]1[CH:27]=[CH:28][C:21]([Cl:20])=[CH:22][C:23]=1[N:29]1[CH:33]=[N:32][CH:31]=[N:30]1)([CH3:16])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 585418994-(2-amino-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamineHCID 58542078HCID 58542078, compound

Product 1

HCID 53237606HCID 53237606, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

The 4-(2-amino-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamine (185 mg, 0.72 mmol) and 4-chloro-2-1,2,4-triazol-1-yl-benzaldehyde (150 mg, 0.72 mmol) are combined in methanol (5 mL) and warmed to 65° C. After 18 hours, catalytic TsOH is added and heating is continued at 65° C. for 48 hours. The reaction mixture is cooled to room temperature and concentrated. The residue is purified via flash chromatography (12 g silica gel, 0-10% MeOH/CH2Cl2). Product-containing fractions are combined and concentrated. The residue is diluted with acetonitrile and the resulting solid product is collected via filtration (55 mg, 17%). LCMS (ESMS): m/z 445.20 (M++1)

Workup

  1. temperatureheating
  2. waitis continued at 65° C. for 48 hours
  3. temperatureThe reaction mixture is cooled to room temperature
  4. concentrationconcentrated
  5. customThe residue is purified via flash chromatography (12 g silica gel, 0-10% MeOH/CH2Cl2)
  6. concentrationconcentrated
  7. additionThe residue is diluted with acetonitrile
  8. filtrationthe resulting solid product is collected via filtration (55 mg, 17%)

Sources & evidence

ORD record
ord-22fbcaf074a2482f89294f06db10655f
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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