Triethylamine → HCID 117839810, compound

HRID 1477682Notes

Reaction equation

HRID 1477682 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[N:13]=[C:12]([CH3:14])[N:11]([CH2:15][C:16]3[S:17][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:20]=3)[C:10](=[O:25])[N:9]=2)[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>ClCCl.O>[CH3:33][S:34]([O:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]2[N:13]=[C:12]([CH3:14])[N:11]([CH2:15][C:16]3[S:17][C:18]([C:21]([F:23])([F:22])[F:24])=[CH:19][CH:20]=3)[C:10](=[O:25])[N:9]=2)[CH2:6][CH2:7]1)(=[O:36])=[O:35]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 117839477HCID 117839477, compound

Product 1

HCID 117839810HCID 117839810, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a dichloromethane solution (2.0 mL) of 4-(4-hydroxypiperidin-1-yl)-6-methyl-1-{[5-(trifluoromethyl)thiophen-2-yl]methyl}-1,3,5-triazin-2(1H)-one (374 mg, 1.00 mmol) synthesized in Reference Synthesis Example 348 and triethylamine (557 μL, 4.00 mmol), methanesulfonyl chloride (155 μL, 2.00 mmol) was added dropwise at 0° C. and the resultant mixture was stirred at room temperature for 1 hour. After the reaction, water was added to the reaction solution and extraction from the resultant mixture with dichloromethane was performed. The obtained organic layer was dried over anhydrous sodium sulfate and thereafter concentrated under reduced pressure to obtain the title compound (453 mg, yield 100%).

Workup

  1. additionwas added dropwise at 0° C.
  2. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b517a8c10b3641eda1485f45295367db
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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