Triethylamine → HCID 71475708, compound

HRID 629925Notes

Reaction equation

HRID 629925 reaction equation
[CH3:1][C:2]([CH3:20])([CH3:19])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([CH2:13][CH2:14][CH2:15]O)=[CH:10][CH:11]=2)[N:6]([CH3:17])[C:5]1=[O:18].C(N(CC)CC)C.CS(Cl)(=O)=O.[CH3:33][S:34]([N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1)(=[O:36])=[O:35]>O1CCOCC1>[CH3:1][C:2]([CH3:20])([CH3:19])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([CH2:13][CH2:14][CH2:15][N:40]3[CH2:41][CH2:42][N:37]([S:34]([CH3:33])(=[O:36])=[O:35])[CH2:38][CH2:39]3)=[CH:10][CH:11]=2)[N:6]([CH3:17])[C:5]1=[O:18]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 7091611-(Methylsulfonyl)piperazineHCID 71140761HCID 71140761, compound

Product 1

HCID 71475708HCID 71475708, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 37-2 (0.05 g, 0.18 mmol) in dioxane (1 mL) was added triethylamine (0.10 mL, 0.72 mmol) and methanesulfonyl chloride (0.017 mL, 0.21 mmol). To this resulting mixture was added 1-methanesulfonyl-piperazine (0.09 g, 0.54 mmol) and the reaction was heated to 100° C. for 3 days. The reaction was concentrated and flash column separation using a 0-5% methanol/dichloromethane gradient gave 37-3. (0.025 g, 33%). HRMS (M+H)+: observed=424.2378, calculated=424.2377

Workup

  1. concentrationThe reaction was concentrated
  2. customflash column separation
  3. customgave 37-3

Sources & evidence

ORD record
ord-0445195bb1474a638911c16916e9f8d0
Source dataset
uspto-grants-2016_04
Patent number
US09315518B2

Reaction notes

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