4-Toluenesulfonyl chloride → HCID 118079730, compound

HRID 1485732Notes

Reaction equation

HRID 1485732 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[NH2:12][C:13]1[CH:18]=[C:17]([Br:19])[N:16]=[CH:15][C:14]=1[NH:20][C@@H:21]([CH3:24])[CH2:22][OH:23]>N1C=CC=CC=1>[Br:19][C:17]1[CH:18]=[C:13]([NH:12][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[C:14]([NH:20][C@@H:21]([CH3:24])[CH2:22][OH:23])=[CH:15][N:16]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chloride2×HCID 118078852HCID 118078852, compound

Product 1

HCID 118079730HCID 118079730, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

p-Toluenesulfonyl chloride (0.022 g, 0.114 mmol) was added to a 0° C. solution of (S)-2-(4-amino-6-bromopyridin-3-ylamino)propane-1-ol (0.028 g, 0.114 mmol) in pyridine (2.0 mL). The reaction mixture stirred at 0° C. and was allowed to warm to room temperature over 16 h. A second portion of p-toluenesulfonyl chloride (0.022 g, 0.114 mmol) was added, and the mixture stirred at room temperature overnight. The mixture was concentrated and the residue was partitioned between ethyl acetate and water. The aqueous phase was separated and extracted with ethyl acetate. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford a purple solid. This material was purified via column chromatography on silica gel (Biotage 10 g column, gradient elution with 0-5% methanol-ethyl acetate) to afford (S)-N-(2-bromo-5-(1-hydroxypropan-2-ylamino)pyridin-4-yl)-4-methylbenzenesulfonamide (0.022 g, 48%) as a purple solid. MS (ESI, pos. ion) m/z 400, 402.

Workup

  1. temperatureto warm to room temperature over 16 h
  2. stirringthe mixture stirred at room temperature overnight
  3. concentrationThe mixture was concentrated
  4. customthe residue was partitioned between ethyl acetate and water
  5. customThe aqueous phase was separated
  6. extractionextracted with ethyl acetate
  7. washThe combined organic phases were washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto afford a purple solid
  12. customThis material was purified via column chromatography on silica gel (Biotage 10 g column, gradient elution with 0-5% methanol-ethyl acetate)

Sources & evidence

ORD record
ord-ff635f8b68e94d0a80570237c1024448
Source dataset
uspto-grants-2016_08
Patent number
US09422281B2

Reaction notes

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