4-Methoxybenzylamine → HCID 68328342, compound

HRID 634249Notes

Reaction equation

Cl[C:2]1[N:6]=[C:5]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][CH:11]=[CH:10]3)[S:4][N:3]=1.[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH2:23])=[CH:20][CH:19]=1>CS(C)=O>[NH:12]1[C:13]2[C:9](=[CH:8][C:7]([C:5]3[S:4][N:3]=[C:2]([NH:23][CH2:22][C:21]4[CH:24]=[CH:25][C:18]([O:17][CH3:16])=[CH:19][CH:20]=4)[N:6]=3)=[CH:15][CH:14]=2)[CH:10]=[CH:11]1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 3-chloro-5-(1H-indol-5-yl)-1,2,4-thiadiazole (0.67 g, 2.85 mmol) and 4-methoxybenzylamine (1.95 g, 14.25 mmol, Aldrich) in DMSO (7 mL) was stirred for 12 h at 110° C. The reaction was cooled to RT and quenched with ice cold water (50 mL) and extracted into EtOAc (20 mL). The aqueous layer was back extracted with EtOAc (20 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by using silica-gel column chromatography (eluent: 30-40% EtOAc and petroleum ether) to give 5-(1H-indol-5-yl)-N-(4-methoxybenzyl)-1,2,4-thiadiazol-3-amine (670 mg, 70.5%) as a off brown solid. MS (ESI, pos. ion) m/z: 337.1 (M+1); 1H-NMR (300 MHz, CDCl3): δ 8.44 (brs, 1H), 8.21 (d, J=9 Hz, 1H), 7.73 (dd, J=8.4, 1.8 Hz, 1H), 7.45 (d, J=8.4 Hz, 1H), 7.35 (d, J=8.7 Hz, 2H), 7.28-7.26 (m, 1H), 6.90 (dd, J=6.9, 2.1 Hz, 2H), 6.64 (m, 1H), 5.42 (m, 1H), 4.62 (d, J=7.6 Hz, 1H), 3.80 (s, 3H).

Workup

temperatureThe reaction was cooled to RT
customquenched with ice cold water (50 mL)
extractionextracted into EtOAc (20 mL)
extractionThe aqueous layer was back extracted with EtOAc (20 mL)
dry with materialThe combined organic layers were dried over anhydrous Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified

Sources & evidence

ORD record: ord-e3ff0bedb92c42198e6eed9237acc064
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321756B2

Reaction notes

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