Potassium Carbonate → (S)-N-(2-(4-fluorophenyl)propyl)-3-(3-methoxybenzyl)-1,2,4-thiadiazol-5-amine

HRID 922698Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([CH3:11])[CH2:9][NH2:10])=[CH:4][CH:3]=1.Cl[C:13]1[S:17][N:16]=[C:15]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=2)[N:14]=1.C([O-])([O-])=O.[K+].[K+]>CN1C(=O)CCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([CH3:11])[CH2:9][NH:10][C:13]2[S:17][N:16]=[C:15]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=3)[N:14]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 180 °C

Procedure

To a solution of (S)-2-(4-fluorophenyl)propan-1-amine (96 mg, 0.62 mmol, 1.5 equiv) and 5-chloro-3-(3-methoxybenzyl)-1,2,4-thiadiazole (100 mg, 0.42 mmol, 1.0 equiv) in NMP (0.8 mL) in a microwavable vial was added K2CO3 (230 mg, 1.68 mmol, 4.0 equiv). The mixture was heated by microwave for 15 minutes at 180° C. and then allowed to cool to room temperature. Purification by silica gel across a gradient of 10-30% EtOAc/Hexanes provided the title compound (126 mg, 84%). m/z=358.0 [M+H]+.

Workup

temperatureto cool to room temperature
customPurification by silica gel across a gradient of 10-30% EtOAc/Hexanes

Sources & evidence

ORD record: ord-ee1ae8dc6d8542f0b02b005eb73be788
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278962B2

Reaction notes

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