Triethylamine → HCID 21084040, compound

HRID 347930Notes

Reaction equation

HRID 347930 reaction equation
[O:1]=[C:2]1[N:7]([CH2:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[C:6]2[S:15][C:16]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:5]=2[CH:4]=[CH:3]1.C(N(CC)CC)C.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>C(Cl)Cl.[Cl-].[Na+].O>[CH3:36][S:37]([N:12]1[CH2:13][CH2:14][CH:9]([CH2:8][N:7]2[C:2](=[O:1])[CH:3]=[CH:4][C:5]3[C:17]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)=[C:16]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[S:15][C:6]2=3)[CH2:10][CH2:11]1)(=[O:39])=[O:38]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21084029HCID 21084029, compound

Product 1

HCID 21084040HCID 21084040, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

The compound of Example 118 (104 mg, 0.26 mmol) was dissolved in DCM (5 mL) and triethylamine (73 μL) followed by methanesulphonylchloride (40 μL, 0.28 mmol) added. The reaction was allowed to stir at ambient temperature for 18 hours. The reaction was diluted with brine and extracted with DCM (×3). The organic phases were washed with saturated NaHCO3 solution and dried (MgSO4). The reaction was filtered and the solvents removed in vacuo to give the title product as a white solid (120 mg). δH (CDCl3) 7.45–7.30 (3H, m), 7.27–7.10 (3H, m), 6.43 (1H, d, J 9.4 Hz), 4.12 (2H, q, J 7.1 Hz), 4.02 (2H, d, J 7.2 Hz), 3.75 (2H, m), 2.70 (3H, s), 2.61 (2H, m), 2.20 (1H, m), 1.82 (2H, m), 1.55 (2H, m), 1.12 (3H, t, J 7.1 Hz). LCMS (ES+) RT 3.55 minutes, 475 (M+H)+

Workup

  1. additionadded
  2. extractionextracted with DCM (×3)
  3. washThe organic phases were washed with saturated NaHCO3 solution
  4. dry with materialdried (MgSO4)
  5. filtrationThe reaction was filtered
  6. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-f2b79dd670f64a18b88cf599046b73dd
Source dataset
uspto-grants-2007_02
Patent number
US07176215B2

Reaction notes

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