Triethylamine → 5-(1-ethylsulfonyl-3,6-dihydro-2H-pyridin-4-yl)-3-(5-phenyl-1,2,4-oxadiazol-3-yl)pyrazin-2-amine

HRID 1959418Notes

Reaction equation

HRID 1959418 reaction equation
[CH2:1]([S:3](Cl)(=[O:5])=[O:4])[CH3:2].C(N(CC)CC)C.[C:14]1([C:20]2[O:24][N:23]=[C:22]([C:25]3[C:26]([NH2:37])=[N:27][CH:28]=[C:29]([C:31]4[CH2:32][CH2:33][NH:34][CH2:35][CH:36]=4)[N:30]=3)[N:21]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>ClCCl>[CH2:1]([S:3]([N:34]1[CH2:35][CH:36]=[C:31]([C:29]2[N:30]=[C:25]([C:22]3[N:21]=[C:20]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[O:24][N:23]=3)[C:26]([NH2:37])=[N:27][CH:28]=2)[CH2:32][CH2:33]1)(=[O:5])=[O:4])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 667444423-(5-Phenyl-1,2,4-oxadiazol-3-yl)-5-(1,2,3,6-tetrahydropyridin-4-yl)pyrazin-2-amine

Product 1

HCID 667444435-(1-ethylsulfonyl-3,6-dihydro-2H-pyridin-4-yl)-3-(5-phenyl-1,2,4-oxadiazol-3-yl)pyrazin-2-amineYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethanesulfonyl chloride (62.13 mg, 45.78 μL, 0.4832 mmol) and triethyl amine (122.2 mg, 168.3 μL, 1.208 mmol) were added to a solution of 3-(5-phenyl-1,2,4-oxadiazol-3-yl)-5-(1,2,3,6-tetrahydropyridin-4-yl)pyrazin-2-amine (129 mg, 0.4027 mmol) in dichloromethane (5 mL) at 0° C. and the resulting solution stirred at room temperature for 2 h. The reaction mixture was concentrated in vacuo and purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were collected, and freeze-dried. The solid was taken up in dichloromethane (5 mL) and washed with saturated aqueous NaHCO3 solution (2×5 mL), dried over MgSO4 and concentrated in vacuo to leave the product (65 mg, 40% yield) 1H NMR (400 MHz, DMSO) d 1.24 (t, 3H), 2.68 (m, 2H), 3.13 (q, 2H), 3.48 (m, 2H), 3.99 (m, 2H), 6.63 (m, 1H), 7.29 (br s, 2H), 7.68 (m, 2H), 7.77 (m, 1H), 8.26 (m, 2H) and 8.52 (1H, s) ppm; MS (ES+) 412.97

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]
  3. customThe fractions were collected
  4. customfreeze-dried
  5. washwashed with saturated aqueous NaHCO3 solution (2×5 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d7f27f505615418094d28da65dfaacac
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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