Triethylamine → HCID 86623366, compound

HRID 2189244Notes

Reaction equation

HRID 2189244 reaction equation
[NH2:1][C:2]1[C:7]2[N:8]=[C:9]([S:15][C:16]3[C:24]([Br:25])=[CH:23][C:19]4[O:20][CH2:21][O:22][C:18]=4[CH:17]=3)[N:10]([CH2:11][CH2:12][CH2:13][OH:14])[C:6]=2[CH:5]=[CH:4][N:3]=1.CCN(CC)CC.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>O1CCOCC1>[CH3:33][S:34]([O:14][CH2:13][CH2:12][CH2:11][N:10]1[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH2:1])[C:7]=2[N:8]=[C:9]1[S:15][C:16]1[C:24]([Br:25])=[CH:23][C:19]2[O:20][CH2:21][O:22][C:18]=2[CH:17]=1)(=[O:36])=[O:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68931300HCID 68931300, compound

Product 1

HCID 86623366HCID 86623366, compoundYield 45,707.699%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

Compound 0403-51 (264 mg, 0.624 mmol) was dissolved in hot anhydrous dioxane (8.6 mL). The solution was cooled to 40° C. and was treated with NEt3 (189 mg, 1.87 mmol) and MsCl (107 mg, 0.935 mmol) for 20 min. The mixture was concentrated and purified by column chromatography on silica gel (CH2Cl2/MeOH=50/1) to give the title compound 0404-51 as a white solid (143 g, 50%): LCMS: 501 [M+1]+.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by column chromatography on silica gel (CH2Cl2/MeOH=50/1)

Sources & evidence

ORD record
ord-9940ade03dec4b19b5cf31f25aaa15ec
Source dataset
uspto-grants-2012_12
Patent number
US08324240B2

Reaction notes

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