4-Toluenesulfonyl chloride → HCID 66690768, compound

HRID 337151Notes

Reaction equation

HRID 337151 reaction equation
[CH:1]1([NH:4][C:5](=[O:35])[C:6]2[CH:11]=[C:10]([N:12]3[CH:17]=[CH:16][N:15]=[C:14]([NH:18][C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[S:28][CH2:29][CH2:30]O)([CH3:21])[CH3:20])[C:13]3=[O:32])[C:9]([CH3:33])=[C:8]([F:34])[CH:7]=2)[CH2:3][CH2:2]1.Cl.C(N(CC)CC)C.C1(C)C=CC(S([Cl:53])(=O)=O)=CC=1.[Cl-].[Li+]>C(#N)C.O.C(N(CC)CC)C>[Cl:53][CH2:30][CH2:29][S:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:19]([NH:18][C:14]1[C:13](=[O:32])[N:12]([C:10]2[CH:11]=[C:6]([CH:7]=[C:8]([F:34])[C:9]=2[CH3:33])[C:5]([NH:4][CH:1]2[CH2:3][CH2:2]2)=[O:35])[CH:17]=[CH:16][N:15]=1)([CH3:21])[CH3:20]

Participants

8

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 11130Triethylamine hydrochlorideHCID 433294Lithium ChlorideHCID 66688879HCID 66688879, compound

Product 1

HCID 66690768HCID 66690768, compoundYield 94.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

A solution of N-cyclopropyl-3-fluoro-5-{3-[(1-{2-[(2-hydroxyethyl)sulfanyl]phenyl}-1-methylethyl)amino]-2-oxopyrazin-1(2H)-yl}-4-methylbenzamide (Example 320g, 0.15 g) dissolved in acetonitrile (2 mL) was treated with triethylamine (0.048 mL) and triethylamine hydrochloride (4.16 mg) under nitrogen. The resulting solution was stirred at 0° C. before adding p-toluenesulfonyl chloride (0.055 g) over 5 min. Lithium chloride (0.064 g) was then added and the mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with water (200 mL), and extracted with DCM (200 mL). The organic layer was separated, dried (MgSO4) and evaporated to afford the subtitle compound (0.14 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 16 h
  2. extractionextracted with DCM (200 mL)
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-0464e6a57c724b299a8eae8f70308847
Source dataset
uspto-grants-2014_11
Patent number
US08889692B2

Reaction notes

Loading…