Triethylamine → HCID 46851731, compound

HRID 241641Notes

Reaction equation

HRID 241641 reaction equation
[NH:1]1[CH2:4][CH:3]([CH2:5][S:6]([C:9]2[CH:26]=[CH:25][C:12]3[N:13]([CH2:21][CH:22]4[CH2:24][CH2:23]4)[C:14]([CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[N:15][C:11]=3[CH:10]=2)(=[O:8])=[O:7])[CH2:2]1.C(N(CC)CC)C.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>ClCCl>[CH:22]1([CH2:21][N:13]2[C:12]3[CH:25]=[CH:26][C:9]([S:6]([CH2:5][CH:3]4[CH2:2][N:1]([S:35]([CH3:34])(=[O:37])=[O:36])[CH2:4]4)(=[O:8])=[O:7])=[CH:10][C:11]=3[N:15]=[C:14]2[CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:23][CH2:24]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58513592HCID 58513592, compound

Product 1

HCID 46851731HCID 46851731, compoundYield 59.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(azetidin-3-ylmethylsulfonyl)-1-(cyclopropylmethyl)-2-neopentyl-1H-benzo[d]imidazole (STEP F of Example 3, 350 mg, 0.780 mmol) and triethylamine (395 microL, 2.81 mmol) in dichloromethane (10 mL) was added methanesulfonyl chloride (67.0 microL, 0.819 mmol) and stirred for 3 h at room temperature. The reaction mixture was concentrated in vacuo, extracted with ethyl acetate (15 mL) and water (30 mL). The organic layer was dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by silica gel column chromatography (dichloromethane-methanol=100:0 to 100:6). T he resulting product was recrystallized with ethanol (6 mL)-ethyl acetate (1 mL) to give the title compound (212 mg) as pale yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. extractionextracted with ethyl acetate (15 mL) and water (30 mL)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by silica gel column chromatography (dichloromethane-methanol=100:0 to 100:6)
  6. customT he resulting product
  7. customwas recrystallized with ethanol (6 mL)-ethyl acetate (1 mL)

Sources & evidence

ORD record
ord-39f5c1f1eaaa407ebad91e27bee6787c
Source dataset
uspto-grants-2014_02
Patent number
US08653063B2

Reaction notes

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