4-Toluenesulfonyl chloride → HCID 11988575, compound

HRID 1157682Notes

Reaction equation

HRID 1157682 reaction equation
[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([NH:11][CH2:12][C:13]([CH3:24])([CH3:23])[CH2:14][CH:15](O)[C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].S(Cl)(C1C=CC(C)=CC=1)(=O)=O>N1C=CC=CC=1>[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([N:11]2[CH2:12][C:13]([CH3:24])([CH3:23])[CH2:14][CH:15]2[C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chloride2×HCID 59511943HCID 59511943, compound

Product 1

HCID 11988575HCID 11988575, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
100 °C

Procedure

To a solution of 2-chloro-4-(4-hydroxy-2,2-dimethyl-4-pyridin-3-yl-butylamino)-3-methyl-benzonitrile (570 mg, 1.66 mmol) in pyridine (2.3 mL) add tosyl chloride (950 mg, 4.98 mmol) in pyridine (1.2 mL) at room temperature. Heat the reaction mixture at 100° C. for 24 h, add additional tosyl chloride (950 mg), and heat for 24 h at 100° C. Cool to room temperature and concentrate under vacuum. Dissolve the residue in ethyl acetate and wash with water. Dry the organic layer over anhydrous sodium sulfate and concentrate to obtain a brown oil. Purify the oil by silica gel chromatography and preparative HPLC to obtain the title compound. Mass spectrum (m/e): 326 (M+H).

Workup

  1. temperatureheat for 24 h at 100° C
  2. temperatureCool to room temperature
  3. concentrationconcentrate under vacuum
  4. dissolutionDissolve the residue in ethyl acetate
  5. washwash with water
  6. dry with materialDry the organic layer over anhydrous sodium sulfate
  7. concentrationconcentrate
  8. customto obtain a brown oil
  9. customPurify the oil by silica gel chromatography and preparative HPLC

Sources & evidence

ORD record
ord-bc71e0bb4737412baa989d6b138796f6
Source dataset
uspto-grants-2010_10
Patent number
US07807691B2

Reaction notes

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