Triethylamine → HCID 25182416, compound

HRID 1467863Notes

Reaction equation

HRID 1467863 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:32])[C:7]=1[CH2:8][CH:9]([O:20][C:21](=[O:31])[CH:22]([C:24]1[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=1)[CH3:23])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1.C(N(CC)CC)C.[CH3:40][S:41](Cl)(=[O:43])=[O:42]>C(Cl)Cl.O>[Cl:32][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[C:7]=1[CH2:8][CH:9]([O:20][C:21](=[O:31])[CH:22]([C:24]1[CH:25]=[CH:26][C:27]([NH:30][S:41]([CH3:40])(=[O:43])=[O:42])=[CH:28][CH:29]=1)[CH3:23])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58302892HCID 58302892, compound

Product 1

HCID 25182416HCID 25182416, compoundYield 36.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Compound 16 (26 mg, 0.05 mmoles) is dissolved in dry CH2Cl2 (10 mL) under nitrogen atmosphere. The solution is cooled to 0° C. and triethylamine (0.009 mL, 0.066 mmoles) and methanesulphonyl chloride (0.0052 mL, 0.06 mmoles) are added. The mixture is then allowed to react at room temperature for 17 hours. The reaction mixture is then diluted with water (15 mL) and extracted with AcOEt (2×30 mL). The organic phase is dried over Na2SO4 and the solvent is evaporated. The crude is purified by preparative HPLC to yield 10 mg of the title compound as a mixture of diastereoisomers.

Workup

  1. customto react at room temperature for 17 hours
  2. extractionextracted with AcOEt (2×30 mL)
  3. dry with materialThe organic phase is dried over Na2SO4
  4. customthe solvent is evaporated
  5. customThe crude is purified by preparative HPLC

Sources & evidence

ORD record
ord-66dfcd1c5bf2430aa1ea5ce2ab32923c
Source dataset
uspto-grants-2015_04
Patent number
US09000177B2

Reaction notes

Loading…