Triethylamine → HCID 11590678, compound

HRID 272299Notes

Reaction equation

HRID 272299 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][N: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:26]=[CH:25][CH:24]=[CH:23][N:22]=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 11559966HCID 11559966, compound

Product 1

HCID 11590678HCID 11590678, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of the compound from example 1 (100 mg, 0.26 mmol) in dichloromethane (3 mL) was added triethylamine (54.4 μL, 0.39 mmol) at room temperature. The solution was cooled to 0° C. and methanesulfonyl chloride (24 μl, 0.31 mmol) was added. The reaction was stirred for a further 45 minutes. The reaction mixture was then diluted with water (5 mL) and stirred vigorously for 5 minutes. The phases were separated and the organic phase concentrated in vacuo to give the crude residue which was azeotroped with ethyl acetate to afford the product as a crystalline solid, 78 mg (65%).

Workup

  1. stirringstirred vigorously for 5 minutes
  2. customThe phases were separated
  3. concentrationthe organic phase concentrated in vacuo
  4. customto give the crude residue which
  5. customwas azeotroped with ethyl acetate

Sources & evidence

ORD record
ord-fae6532fc7a9418aa46ae9ee5a76414e
Source dataset
uspto-grants-2008_11
Patent number
US07456170B2

Reaction notes

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