Triethylamine → HCID 46851729, compound

HRID 241640Notes

Reaction equation

HRID 241640 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.C[Si]([N:38]=[C:39]=[O:40])(C)C>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]([C:39]([NH2:38])=[O:40])[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 70696Trimethylsilyl isocyanateHCID 58513592HCID 58513592, compound

Product 1

HCID 46851729HCID 46851729, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of 5-(azetidin-3-ylmethylsulfonyl)-1-(cyclopropylmethyl)-2-neopentyl-1H-benzo[d]imidazole (STEP F, 350 mg, 0.780 mmol) and triethylamine (395 microL, 2.81 mmol) in dichloromethane (5 mL) was added trimethylsilyl isocyanate (162 microL, 1.02 mmol) at room temperature. The resulting solution was stirred for 1 h. The reaction mixture was concentrated in vacuo. The residue was extracted with ethyl acetate (15 mL) and washed with water (30 mL). The organic layer was dried over magnesium sulfate. The crude product was purified with silica gel column chromatography (ethyl acetate-methanol=100:1 to 100:8) to give the title compound (198 mg, 61%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. extractionThe residue was extracted with ethyl acetate (15 mL)
  3. washwashed with water (30 mL)
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customThe crude product was purified with silica gel column chromatography (ethyl acetate-methanol=100:1 to 100:8)

Sources & evidence

ORD record
ord-d39dc18fe65a4552b0c5822509d2adfa
Source dataset
uspto-grants-2014_02
Patent number
US08653063B2

Reaction notes

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