4-Methoxybenzylamine → 5-(3-iodo-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine

HRID 634132Notes

Reaction equation

[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[S:12][C:13](S(C)=O)=[N:14][N:15]=3)[CH:9]=2)[N:4]([S:19]([C:22]2[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH:3]=1.[CH3:29][O:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35][NH2:36])=[CH:33][CH:32]=1>O1CCOCC1>[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[S:12][C:13]([NH:36][CH2:35][C:34]4[CH:37]=[CH:38][C:31]([O:30][CH3:29])=[CH:32][CH:33]=4)=[N:14][N:15]=3)[CH:9]=2)[N:4]([S:19]([C:22]2[CH:23]=[CH:24][C:25]([CH3:26])=[CH:27][CH:28]=2)(=[O:21])=[O:20])[CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of 2-(3-iodo-1-tosyl-1H-indol-5-yl)-5-(methylsulfinyl)-1,3,4-thiadiazole (423 mg, 0.757 mmol) in dioxane (3.0 mL) was added 4-methoxybenzylamine (0.294 mL, 2.268 mmol) at RT. The reaction was heated at 100° C. for 24 h. The solvent was removed and the residue was sonicated in MeOH and filtered. The filtrate was concentrated and the residue was purified with flash chromatography (eluting with 0-50% EtOAc in DCM) to give 5-(3-iodo-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine (245 mg, 0.397 mmol, 47%). MS (ESI, pos. ion) m/z: 617 (M+1); 1H NMR (400 MHz, DMSO-d6) δ ppm 8.40 (t, J=5.67 Hz, 1H), 8.16 (s, 1H), 8.03 (d, J=8.61 Hz, 1H), 7.94 (d, J=8.41 Hz, 2H), 7.79 (dd, J=8.71, 1.66 Hz, 1H), 7.62 (d, J=1.56 Hz, 1H), 7.42 (d, J=8.41 Hz, 2H), 7.32 (d, J=8.61 Hz, 2H), 6.92 (d, J=8.61 Hz, 2H), 4.46 (d, J=5.67 Hz, 2H), 3.73 (s, 3H), 2.33 (s, 3H).

Workup

customThe solvent was removed
customthe residue was sonicated in MeOH
filtrationfiltered
concentrationThe filtrate was concentrated
customthe residue was purified with flash chromatography (eluting with 0-50% EtOAc in DCM)

Sources & evidence

ORD record: ord-32dc7f2319b3403da577a11980d43cbd
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321756B2

Reaction notes

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