Lawesson's reagent → {4-[5-(4-Benzyloxy-3-ethyl-5-methyl-phenyl)-[1,3,4]thiadiazol-2-yl]-6-methyl-pyridin-2-yl}-diethyl-amine

HRID 2047333Notes

Reaction equation

[CH2:1]([N:3]([CH2:34][CH3:35])[C:4]1[CH:9]=[C:8]([C:10]([NH:12][NH:13][C:14](=O)[C:15]2[CH:20]=[C:19]([CH3:21])[C:18]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[C:17]([CH2:30][CH3:31])[CH:16]=2)=O)[CH:7]=[C:6]([CH3:33])[N:5]=1)[CH3:2].C(N(CC)C1C=C(C2OC(C3C=C(C)C(O)=C(CC)C=3)=NN=2)C=C(C)N=1)C.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:72])=CC=1>C1COCC1.CC(=O)OCC>[CH2:23]([O:22][C:18]1[C:19]([CH3:21])=[CH:20][C:15]([C:14]2[S:72][C:10]([C:8]3[CH:7]=[C:6]([CH3:33])[N:5]=[C:4]([N:3]([CH2:1][CH3:2])[CH2:34][CH3:35])[CH:9]=3)=[N:12][N:13]=2)=[CH:16][C:17]=1[CH2:30][CH3:31])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 4-benzyloxy-3-ethyl-5-methyl-benzoic acid N′-(2-diethylamino-6-methyl-pyridine-4-carbonyl)-hydrazide (1.29 g, 2.72 mmol, intermediate from Example 81 step a)) in THF (15 mL), Lawesson reagent (1.21 g, 2.99 mmol) is added. The mixture is stirred at 110° C. for 15 min under microwave irradiation (300 W, external cooling). The mixture is cooled to rt, diluted with EA (100 mL) and washed with sat. aq. Na2CO3-solution (3×50 mL) followed by brine (1×50 mL). The org. extract is dried over MgSO4, filtered, concentrated and dried to give crude {4-[5-(4-benzyloxy-3-ethyl-5-methyl-phenyl)-[1,3,4]thiadiazol-2-yl]-6-methyl-pyridin-2-yl}-diethyl-amine (2.43 g) as a yellow oil; LC-MS: tR=1.01 min, [M+1]+=473.20.

Workup

temperatureThe mixture is cooled to rt
washwashed with sat. aq. Na2CO3-solution (3×50 mL)
extractionextract
dry with materialis dried over MgSO4
filtrationfiltered
concentrationconcentrated
customdried

Sources & evidence

ORD record: ord-e81aa6704d464ae6ba294ca9aa1f442c
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592460B2

Reaction notes

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