Triethylamine → HCID 11539825, compound

HRID 272300Notes

Reaction equation

HRID 272300 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([N:15]4[CH2:20][CH2:19][CH:18]([C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=5)[CH2:17][CH2:16]4)=[N:13][N:14]=[C:10]3[CH2:9][NH:8][CH2:7][C:6]=2[CH:27]=1.C(N(CC)CC)C.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>ClCCl.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([N:15]4[CH2:20][CH2:19][CH:18]([C:21]5[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=5)[CH2:17][CH2:16]4)=[N:13][N:14]=[C:10]3[CH2:9][N:8]([S:36]([CH3:35])(=[O:38])=[O:37])[CH2:7][C:6]=2[CH:27]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11696573HCID 11696573, compound

Product 1

HCID 11539825HCID 11539825, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of the compound from example 5 (200 mg, 0.53 mmol) in dichloromethane (5 mL) was added triethylamine (110 μL, 0.79 mmol). The reaction was cooled to 0° C. and methanesulfonyl chloride (48.9 μL, 0.63 mmol) was added. The solution was stirred for 1 hour at room temperature and diluted with water (5 mL). The phases were separated and the organic phase was washed with brine, dried over magnesium sulfate and concentrated in vacuo and azeotroped with ethyl acetate to give the product as a white crystalline solid, 196 mg (76%).

Workup

  1. customThe phases were separated
  2. washthe organic phase was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customazeotroped with ethyl acetate

Sources & evidence

ORD record
ord-52b265edae9a41e49bb56b2720f49e77
Source dataset
uspto-grants-2008_11
Patent number
US07456170B2

Reaction notes

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