4-Toluenesulfonyl chloride → HCID 66690768, compound

HRID 2070830Notes

Reaction equation

HRID 2070830 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-6cca53ce18fe4d5abb42e8c38cf3762b
Source dataset
uspto-grants-2012_10
Patent number
US08299246B2

Reaction notes

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