Triethylamine → HCID 46851730, compound

HRID 241643Notes

Reaction equation

HRID 241643 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([CH2:17][CH:18]4[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]4)(=[O:16])=[O:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:3][CH2:2]1.Cl.Cl[C:31]1[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=1.C(N(CC)CC)C>C(O)C>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([CH2:17][CH:18]4[CH2:19][CH2:20][N:21]([C:31]5[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=5)[CH2:22][CH2:23]4)(=[O:15])=[O:16])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 818524-Chloropyridine hydrochlorideHCID 58513582HCID 58513582, compound

Product 1

HCID 46851730HCID 46851730, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 1-(cyclopropylmethyl)-2-neopentyl-5-(piperidin-4-ylmethylsulfonyl)-1H-benzo[d]imidazole (STEP D, 25 mg, 0.062 mmol), 4-chloropyridine hydrochloride (19 mg, 0.12 mmol) and triethylamine (35 microL, 0.25 mmol) in ethanol was stirred at 150° C. under microwave for 3 h. The solvent was removed. The residue was diluted with ethyl acetate and saturated sodium bicarbonate aqueous solution to separate. The aqueous layer was extracted with ethyl acetate (3 mL×2) and the organic layer was filtered through magnesium sulfate column. The filtrate was concentrated in vacuo. The residue was purified by prep-LC-MS (“process A”).

Workup

  1. customThe solvent was removed
  2. additionThe residue was diluted with ethyl acetate and saturated sodium bicarbonate aqueous solution
  3. customto separate
  4. extractionThe aqueous layer was extracted with ethyl acetate (3 mL×2)
  5. filtrationthe organic layer was filtered through magnesium sulfate column
  6. concentrationThe filtrate was concentrated in vacuo
  7. customThe residue was purified by prep-LC-MS (“process A”)

Sources & evidence

ORD record
ord-f0349c76be3e48e1819eede1bd8cff46
Source dataset
uspto-grants-2014_02
Patent number
US08653063B2

Reaction notes

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