Lawesson's reagent → HCID 86659538, compound

HRID 1970804Notes

Reaction equation

HRID 1970804 reaction equation
[CH2:1]([C:8]1[C:9]([NH:22][C:23](=O)[CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[N:10][CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:43])=CC=1>C1(C)C=CC=CC=1>[CH2:1]([C:8]1[C:9]([NH:22][C:23](=[S:43])[CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[N:10][CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 46853647HCID 46853647, compound

Product 1

HCID 86659538HCID 86659538, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under an argon atmosphere, 3-benzyl-5-(4-methoxyphenyl)-2-[(4-methoxyphenyl)acetylamino]pyrazine (c-43) (prepared by the method described in Inouye, S. & Hosoya, T., Biochem. Biophys. Res. Commun., 386, 617-622 (2009)) (1.00 g, 2.28 mmol) was suspended in anhydrous toluene (30 mL) and to this was added Lawesson's reagent (552 mg, 1.37 mmol) while stirring at room temperature, and then heated to reflux for 17 h. After refluxing, it was cooled to room temperature, and concentrated under reduced pressure with a rotary evaporator. The residue was purified by silica gel column chromatography (100 g, dichloromethane/ethyl acetate=49/1) to give 3-benzyl-5-(4-methoxyphenyl)-2-[(4-methoxyphenyl)thioacetylamino]pyrazine (c-44) as a yellow oily substance (823 mg, 79.4%). Rf=0.43 (dichloromethane/ethyl acetate=19/1). 1H NMR (400 MHz, DMSO-d6) δ 2.84 (s, 3H), 3.82 (s, 3H), 3.92 (s, 2H), 4.07 (s, 2H), 6.90-6.96 (AA′BB′, 2H), 6.98-7.04 (AA′BB′, 2H), 7.05-7.11 (AA′BB′, 2H), 7.13-7.26 (m, 3H), 7.38-7.50 (m, 2H), 8.06-8.11 (AA′BB′, 2H), 8.99 (s, 1H), 12.12 (s, 1H). 13C NMR (67.8 MHz, DMSO-d6) δ 39.3, 50.8, 55.0, 55.3, 113.8 (2C), 114.5 (2C), 126.3, 127.6, 128.18 (2C), 128.21 (2C), 128.8, 128.9 (2C), 130.0 (2C), 137.8, 138.0, 145.0, 149.6, 152.1, 158.4, 160.8, 205.1. IR (KBr, cm−1) 704, 835, 1030, 1113, 1175, 1250, 1292, 1304, 1319, 1371, 1422, 1439, 1493, 1510, 1607, 2835, 2932, 2957, 3150. HRMS (ESI+) m/z 456.1747 ((M+H)+, C27H26N3O2S+ requires 456.1740).

Workup

  1. temperatureheated
  2. temperatureto reflux for 17 h
  3. temperatureAfter refluxing
  4. temperatureit was cooled to room temperature
  5. concentrationconcentrated under reduced pressure with a rotary evaporator
  6. customThe residue was purified by silica gel column chromatography (100 g, dichloromethane/ethyl acetate=49/1)

Sources & evidence

ORD record
ord-8a8508a79e4646ff97b32aad659d5b6c
Source dataset
uspto-grants-2013_04
Patent number
US08431525B2

Reaction notes

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